1. Seemless integration with online banking service to pull down transactions
2. Ability to import my transaction history from Microsoft Money (and import it pretty easily)
3. Ability to preserve my categories after import
4. Ability to preserve my transfer transactions (for reporting purposes) between accounts
5. Ability to setup recurring transactions for bills, paychecks and things that recur.

Failure
I trialed several pieces of Mac money-management software – Moneywell, Moneydance, Money (unrelated to Microsoft Money), iCash, the Quicken Financial Life beta and a few others.  The Apple Mac OS X downloads directory served as a great place to discover software, but some better search capabilities and categorization could be helpful.  After searching, I found that the staff picks are a great guide to the best available titles.

A lot of developers are putting effort into money management on the Mac and there is a diverse group of software out there.  Many of the developers have a different take, a different idea than your traditional, mainstream products.  The downside is that sometimes the software packages are feature limited to the specific idea.   A lot of the software was pretty simple software and much of it was well designed and positively reviewed.   Most of the software is available as shareware or trial-ware, so that you can try before you buy.

So, I chose several of the more mainstream Mac products and gave them a try.  Of the software, I thought Moneywell was the best suited for my needs, so I purchased it and began my conversion.  Money could export the transactions of each account to a QIF file, so I did and then imported into Moneywell.  As I reported, the categories stayed in tact and everything looked good.  I hooked up the accounts to the online banking, downloaded transactions and then hit a problem – I couldn’t reconcile my checkbook.

In MS Money, I’d devised my method for making sure I didn’t overdraft – I pre-entered my transactions. I quickly found that Moneywell didn’t have running balances – only daily balances.  It made it hard to reconile and I was too accustomed to MS Money, so I switched back in a few days and continued to try to work with Moneywell.

Before I knew it, weeks had gone by.  So, I worked hard, reconciled everything and tried again to use Moneywell again.  For some reason, duplicate and extra transactions continued to throw off my balances (because of my pre-entry habit) and I depend heavily on downloaded transactions to fill in the gap.  Fortunately, Moneywell did a better job matching transactions that MS Money ever did, but manually searching for a transaction was too much work.  Moneywell had a reconcile feature which, I’ll admit, I didn’t use.  At the time, I thought reconcile was something you did with paper statement.  I’d later learn (too late) that reconcile could have saved me the entire time.

The other limiting problem was transfers transactions.  The QIF export and import didn’t link accounts and take into consideration my transfers between accounts. I would have needed to go through and manually enter and remove duplicate transactions for four years — not something I was looking forward to.

So, I gave up and continued to use MS Money.

Invitation to switch
Intuit, very smartly, began advertising within the MS Money application that they were offering switchers discounts to move to Quicken.  In addition, they’d invested time doing an almost complete data conversion of MS Money data to Quicken data for the new 2010 version of the Quicken software.  Having failed a manual conversion, I decided to give it a try – it certainly sounded better.  Unfortunately, there was no trial version to try – so I had to dive in and purchase Quicken for Windows 2010.

The data conversion worked as advertised – almost seemlessly.  Within about 15 minutes all of my MS Money history was sitting happily in Quicken.  The interface was completely different, but all of my data seemed to be preserved.  There were a few notes that Quicken handles investment accounts (particularly cash in investment accounts) differently than Money and that I would have to do some manual cleanup for those accounts.  Fortunately, I’m investment lite, so it wasn’t a lot of work.

Of my checklist, Quicken met all 5 points.  All of my transfer transactions were preserved, my categorization was preserved and even my bills reminders were kept and transferred into Quicken recurring transactions.  My account metadata (bank name, account number, etc.) was also preserved and Quicken identified which banks had online services available based on the bank name.  One of my local banks even offered Quicken online services where they weren’t available in MS Money.

Quicken did a good job guiding me through the process of what to do after conversion – including linking the accounts back to online banking.  The vault feature saved individual passwords to banks so that it could automatically update as needed.  In addition, the vault was protected by a master password to keep it nice a secure.  A few minutes later, my account were linked and downloading new data.

But problems arose only a couple days a couple days after the conversion, similar problems that I had experienced in Moneywell.  Transactions weren’t reconciling and matching automatically when downloaded and my running balances were off again.  In addition, most of my 4 years of history weren’t cleared after the conversion.  Great – another failure coming…

First, I tackled the matching transactions.  Automatically entering the downloaded transactions seemed to be the problem, mainly because of pre-entering the transactions.  A quick search online sent me to the Quicken’s preferences and changing the automatic acceptance of transactions so that I can manually match them.  After that preference change, the register looked a lot like Quickbooks register and I could see the downloaded transactions and manually match them when necessary to the register.

To balance and clear my historical transactions, I tried the reconcile feature.  The reconciliation window let me compare money in and money out and make things tie to each other.  Money In = Money Out +/- Balance.  Its a pretty simple concept – and one that I completely missed earlier.  Newly downloaded and matched transactions automatically clear.  I cleared four years of prior transactions and Quicken actually found a discrepancy on one account and automatically entered a balance adjustment to compensate and tie to the online balance – much easier than MS Money.

Moneywell’s reconcile feature might have proved just as effective, if only I had tried it.  But, it was different than my normal mode of operation and so, I didn’t know.  But I should have spent more time reading and researching before giving up.  The transfers are the one problem left on my list for Moneywell and perhaps in the future, I could move to a Mac solution, but for now Quicken is doing the job quite well.

There are some things Quicken does better — in addition to the downloaded transactions and reconciliation features.  The reports are much better and faster than MS Money.  The way that transactions are matched is more intuitive in Quicken rather than matching them in the register, they are neatly kept below the register until all matched.  I also like the investment listing better in Quicken — gone are the integrated MSN Money with ads and other distractions.

All in all, I think Quicken 2010 for Windows is a winner.  Intuit has certainly captialized on the demise of MS Money and provided the easiest path for Money users to switch that I have encountered.  That doesn’t mean that life is without flaws – the best Quicken version and the one I am using is on Windows.

What about Mac software?
The new Quicken Essentials for Mac is no where comparable.  Essentials for Mac is appropriately named since its missing many features and it is a very basic package.  It is, however, very Mac-like and intuitive to use and it will make sense for many Mac users  My hope is that it will grow and mature, but its taken several years to bring it market (currently scheduled for February 2010) — the last revision is from 2007.

The screenshosts posted on the Quicken site look much better than the beta I played with.  And, conversion from your Quicken for Windows is a promised feature, though the list of what can’t be converted from Quicken Windows is pretty long.  For those who need advanced features on Mac, Inuit still recommends Quicken for Mac 2007, which has more features, but looks cludgy to me and still doesn’t have all the features of the Windows version.  The Mac version of Quicken and Quickbooks have always lagged behind their Windows counterparts, but hopefully the resurgence of Mac will help level the playing field.

Quicken for Mac is the most likely path for my next (far in the future) migration once the product has matured, if and when that happens.  I suspect the cloud based solutions like Mint.com will become more popular and desktop software may be pushed out to the pasture.

Unfortunately yes, I am still using Microsoft Money – I can’t break my habits there and Moneywell, albeit nice, has some things that I just can’t get accustomed to.  I really need the running totals on accounts because of the number of transactions that I post each week and missing those makes it very hard to reconcile my accounts.  I think that is the key feature missing for me.  I just wish there was a preference to enable that within the program.  It seems like such an easy feature to add.

I notice too that Quicken is releasing an “Essentials for Mac” package with the new Financial Life, but that won’t meet my needs – particularly on the investment side.  So I am still looking.  I would switch to Mint.com if I were able to import my account histories.  I just have so much past history in my data file that I want to keep for year to year reference and to look back – I hate to abandon it, but I fear that I’ll soon be locked out if I ever have to reinstall MS Money.

I know that I can’t be the only Mac user in the world looking for a suitable money management package.  Its a market which has a bunch of new options – what are some – what are you using?

But it begs the question, why do this?  To answer that, you have to understand that USAA is not your standard bank.  USAA caters mostly to military families and their dependants.  Its members are widespread and not concentrated in any one area (except maybe military bases).  It also has members all around the globe.   USAA doesn’t have physical branches.  Everything is done over the phone or via the internet.

USAA.com is an excellent banking site, the best in my opinion because of the functionality at your reach as a customer.  You can do almost everything you’re normally do after waiting in line at the local branch online.  New accounts are setup online easily and quickly, mortgage applications and more.  USAA is also an investment and insurance carrier and those products are available online.

So, the online deposit wass the next logical extension.  For a bank with no branches and no tellers, extending the convenience of an instant deposit  is great (something, not even available in a local branch — remmber got to wait til 2pm or next day).  Some checks don’t deposit, if they are too light or if they are illegible.  For those, you put it into a postage-paid envelope and mail it off to their processing center.  This was the only method of deposit several years ago when we joined.   USAA has experimented with other methods in the past, including a method utilizing UPS to deliver the deposits overnight.  That trial only lasted a few months, and I can imagine, it was costly for the bank.  Even the snail-mail method only took two to three business days for the deposit to appear.

And I’ve said it before, USAA is a stand-up, top-notch organization and its always a pleasure to do business with them.  They really understand customer service, whether its speaking with you on the phone or whether its extending technology into your hands to better serve you.  So, now I’m awaiting the updated iPhone application (I already have the current one installed!) to try out deposit from iPhone, or whatever they’ll brand it.

Now, a month later, I have a lot of reconciliation to do to catch up in Moneywell.  The thing I am struggling with most in the software are duplicate transactions and how to easily find them.  Running balance is how I’ve always been able to check and make sure everything is on track from day to day, and although the daily totals are in Moneywell, I’m finding it hard to find errors.

And, part of this is self-inflicted (see, really sensing a theme here).  I like to prepopulate my transactions in my financial program and so there are transactions for up to a month in advance in Moneywell.  So when the real transaction downloads and the dollar amounts don’t match from my guestimate transaction, my balances go wonky.

The other thing I miss from Microsoft Money is my bill reminders – my recurring transactions in Quickbooks speak.  I’ve used these to remind me of annual and quarterly bills, plus my monthly transactions. Its kept me honest with the trash company and even helped me make sure I never overdraw the account on a month-to-month basis.

So, back to the drawing board.  I need to carve out some time this week in the evening to get things caught up in Moneywell.  I really believe the software has a lot of promise for me and for my family’s finances.  I need to give it an honest try!

For those in the beta test program, it doesn’t come as much of a surprise.  Quicken Financial Life shows a lot of promise, but many of the features are yet to be implemented.   The release was supposed to come during the summer months of 2009, but any reference to that release have since been hidden on the Intuit website.  Pages of information previewing the release have been removed and the Quicken Blog post is the only source for any current information.

My personal frustration over this release is apparently shared by many users, judging by the comments left on the blog post.  I wonder why it taking so much time to show any real progress in the product.  QIF import, for instance, isn’t implemented making transferring your historical data next to impossible.  The only way to import historical data is upgrading from Quicken for Mac 2007 – which I don’t own.  Capturing what’s left of the switchers, like myself,  is a big way that Intuit could capitalize and profit with this release, but it seems to be ignored.  Oh, well, time will tell.

I’ve covered before how Moneywell handles running balances and accounts.  Something that I haven’t mentioned is that Moneywell has some really good, powerful reconciliation workflows integrated in it.  The Reconcile screens are great for someone who is paper based and who reconciles the checkbook with the printed statements at the end of the month.  But, that’s not me – those aren’t my habits.   And it has to be a system that works with me, else I have to change and the chances of success decrease.

The reconcile functionality appears to be their solution for keeping your checkbook in balance.  For that type of system, I’m sure that it works well and the daily balances make much more sense — see, you’ll have a statement balance to match to every month in that style system.

But, what about someone who uses online banking – particularly someone who does it daily and whose reconciliation process occurs almost as often?  I guess that I could begin matching the running balance online with the daily balance in Moneywell and marking the transactions as reconciled once they hit the online account and clear.  That, I assume, is the same net outcome as reconciling to a paper statement.  So, that is what I am resolving today to attempt for the next week.  I’m going to try and modify my actions and see if I may be able to adopt a better way of accounting my personal finances.

In the meantime, I have been relying too heavily upon Microsoft Money.  I know this and I have paid money for a software which seems to be better long term.  I have to keep this in my mind and remind myself daily to do it.

But right now, I’m at the why doesn’t my new product live up to my old product point and its over running balances.  See, in the Moneywell there aren’t any running totals.  See this screenshot below (from the Moneywell website):

Much of what I like about Moneywell is that they’ve re-thought traditional personal finance software.  But, I used running balances to play what if and make sure I don’t overdraw my accounts by posting upcoming transactions.  I know it seems archaeic but that is how I found best NOT to get into trouble.  Money’s cash flow forecaster was never accurate for me, so I couldn’t rely on it.  I went the more low-tech way and just added transactions and saw what was left.

So, I mentioned the Moneywell is a re-think product and in the case of balance, it rethinks  that too.  If you click on a transaction, in the bottom bar, it shows a daily balance amount for the day of the transaction.  That is great, but its not graphical or easy to see at glace to the “single window” interface.  There is also no “red flag” you’re in trouble indicator for a day, that I’ve found.

So, I’m searching for Moneywell’s better way.  I’m sure its here, but just in case – a cash forecast graph would be a great feature in the next release.  Take that daily balance and graph it…  I haven’t figured out how to read the bar charts at the bottom of the page (nor change them) so maybe that’s what they’re intended for, but if so, its not intuitive and its also not day by day…

I initially had problems and had dimissed Moneywell because I could not connect to my primary bank.  After perusing the Quicken Financial Life forums (I was a beta tester), I found the issue – I was not using the correct username and password.  To work with my bank, I needed to provide my member number and PIN to authenticate – not my website username and password.  Worked that out, and now automatic updates are all set.

After that hurdle was cleared, I found out that already had too many transactions for the trial version.  So, rather than importing and trying anything else, I decided to see how some of the features work.

First, I looked at the categorizations.  These were preserved from Microsoft Money perfectly.  I used the “Loose QIF” export which preserved long category names and transaction titles and Moneywell imported all this information correctly.  I was also able to see graphs by category and subcategory.  One thing different from Microsoft Money is that each subcategory is really a category of its own.  So, as cleanup, I will most likely be combining categories and renaming some.

The category list is excellent when you’re searching for a particular transaction.  If you knew it was from my remodel project, hit my Household:Remodel category and you’d be looking at just those transactions in the account selected.  That’s got a leg up on Microsoft Money already.

The other thing Moneywell includes throughout is search.  And how handy is that for quickly locating a transaction at Lowes or Wal-Mart.  The one gotcha I found was in my method of import.  If I left Moneywell setup the account from my bank online, it would create a Starting Balance transaction.  Once I imported my QIF export from Money, the Starting Balance would throw the totals off – but a quick search, delete and we were back to balanced.

I’m a big fan of the envelope system (Dave Ramsey advocates this system) and Moneywell is based around that system of budgeting.  I really like the way that budgets “Spending Plans” are setup.  That’s a nice, logical system compared to the cumbersome budgets in Microsoft Money – especially the last 3 revisions.  And I know is it essentially the same thing, but a spending plan just sounds better than a budget.   I haven’t completed my budget, but I’ll post about that experience once I tackle that.

In Money, I could never get my budgets to line up and match the reports after I created them.  I also had this problem with extra income showing up in my budgets that wasn’t there.  The extra income was from a previous job, yet Microsoft Money kept bringing it over year after year.

Transfer transactions were an expected problem.  But Moneywell performs better in some respects.  The virtue of the categories, there is a Transfer category preserved from the Money exports.  That makes it easy to identify and remedy the transfer transactions.  The process is two step, however.  You have to identify the transfer transaction, click on each transaction and assign the transfer account – and then you have to go to that account and merge the duplicates.  That merge process is a little tedious, but there is merge functionality in the program – I just need to find out how to initiate a merge.  I have seen it when importing QIF files.

So after my testing, I went ahead and purchased Moneywell – and so far, it feels like Money well spent.  I still have a number of bank accounts to add and lots of cleanup to do.  I also haven’t added my mortgages or investment accounts – so no way of knowing how it will do tracking those – something Money did pretty well.

Any of these companies who could write a Money to {insert product} conversion program could have a really great opportunity to pickup new customers, in my opinion.  But with a small market share, I’m not sure it will happen.

After launching the software last night, an error appeared alerting me that the build expired and to go to Check for Updates to see if a newer build existed.  Problem was the software would not allow you to access the Check for Updates option that the error message references – the program just closed.  I also found my download link had been changed to say that the beta program was full and no longer accepting anyone.

Fine, I knew the program still worked in May when I last used it, so I turned back my clock and sure enough the program fired up.  I was able to check for update – there was not one.  But I also was able to see the community page and a note I’d missed saying that the forums had been closed and no new posts would be allowed.  The Quicken staff promised to go through all feedback left in the forum and it would be left online, as read-only.

So, that’s it for beta testing.  I think the product has a lot of potential.  Unfortuantely, some of the basic functionality – like importing QIF files – was missing.  I think that the simplistic approach that Financial Life is built around is very Mac like and so it feel more like a Mac program than a warmed over Windows version that Quicken for Mac 2007 feels like (don’t own Quicken for Mac, but I have used it).  Ultimately though, the beta version I was testing felt half baked and wasn’t usable for me as a real money management package.    My biggest issue (as with most packages) is getting my historical data – and there was no way for me to that with Financial Life.

I hope that the final release of Financial Life will be on the market soon, but I fear that it will be too feature incomplete to compete with online services and existing software – Moneydance, Moneywell, etc.

Microsoft Money was the one product that I haven’t found a suitable alternative for on the Mac.  And having years of data in its proprietary format doesn’t help, either.  Really, there are great Mac software options, including Quicken for Mac (maybe Quicken Financial Life sometime soon), Moneywell or Moneydance.

My problem is getting my data converted into these products and preserving my budget categories and some of the data consistency I’ve worked hard to put together.  My one gripe across the board with the Mac based money management products is that they don’t offer the seamless online tie in and automatic downloads that Money does – even Quicken.  With Quicken 2007, even though my bank is listed as an automatic download option, my bank’s enhanced security defeats the product’s download function.  Same goes for Moneywell. (UPDATE: Thanks to my Quicken Financial Life beta forum, I was able to find the magic recipe to get online updates working on QFL and Moneywell with my primary bank!)  Mint.com can do it, you should be able too.

What Mint.com doesn’t do it account for my history – my years of prior data.  Same with Quickens Online solution.  I also didn’t like their categorization.  In the least, Quicken online should be able to upload QIF files of all my data to setup my accounts.  I pray that this feature soon comes.

So, I’m stuck.  I have to find something between now and June 2011 when all my much-loved, automatic services go dark.  I’m searching… more soon…