this starts out with the usual talking points about cybersecurity and the relative power of the models under discussion.

it lands in a very different place.

quicken was intuitive (and the company was more or less named along those lines) and it just worked. then along came microsoft money. i, a blue blooded devotee of everything UNIX, embraced that application with both arms and i might have on occasion tried to dry hump it. yes, i loved that app. then $MSFT decided that they were going to kill that product. don’t they know that i ran a special, heavily hardened VM just to have that application at my disposal?

then i tried mint, it was good, but i couldn’t enter transactions manually, the projection and cash flow tools were poor and the budgeting tools were horrid. but, it was free and if you could come to terms with the faustian bargain that was having a 3rd party collect financial information on you, it was reasonably workable. then they got big, their feeds and their back end started to suffer, the customer service interaction was pretty horrid. WTF - forums? i know that’s very web 2.0 but i need to get resolution to these issues, not fuck around in a forum commiserating with a bunch if like-irritated customers. if i give you money to provide me with a reliable, secure and supported service will you hook me up? there’s a lot to love about what you’ve got going there.

then quicken/intuit acquired them and the community puckered up their bungholes. quicken for the mac had been a train wreck, quickbooks is an application that pretty much everybody loathes but there really don’t appear to be better options so everyone just sucks it up and deals. but, there was a contrite blog posting about how mint would be the same old mint it ever was (talk about a mixed message) and this would provide the infusion of cash to make the enhancements, etc. that we’d all been clamoring for, etc. then they added goals, nice. they improved a number of things but you still had the anemic customer care / support and it seemed to require a lot more hand holding than you would expect something along these lines to require.

we plugged along then back in feb / mar time-frame, they made some sort of unholy change to the back end and all hell broke loose. i had dead accounts which couldn’t log in, i was asked to duplicate things, merges were horribly horked up, etc. i gritted my teeth and worked through these issues. this necessitated periodically dealing with erratic duplicate transaction explosions which threw off budget tracking and a host of other things.

then about a month ago i did a little cleanup, following the directions that mint helpfully provided. which i found irritating given that apparently there were enough people experiencing these problems that they had to develop documentation to facilitate manual cleanup on the part of their users. how messed up is that? seriously, you make back end changes to your system and you provide your customers with instructions to address the scorched earth situation that you’ve created? WTF?

following this “clean up”, i was left with a collection of accounts for which i could apparently get budgeting and expense information but i could not see the actual transactions within the accounts. double WTF? i did what you told me to do and you don’t even give me the courtesy of a new opportunity to clean up some freshly created mess? you just hide a bunch of stuff i need, from me, your apparent bitch. well, it’s a free service so it’s not like i’m out any money, just a lot of irritation and time.

so here’s the recurring punchline - i’m quite willing to spend a reasonable amount of money for a solution that works. mint had a good chunk of the stuff that was useful to my household and they were pretty bright about sending me reasonable information on optimizing my finances and usage. i would happily pay a monthly fee for online tools that work and straddle the various accounts that i have spread hither and yon.

now let’s talk about desktop software packages.

after trolling through various software reviews and looking at inscrutable screenshots, perusing feature lists and getting my wife’s input we settled on kicking the tires on a few packages …

MoneyDance 2011 for the mac - sweet they have a demo i can try. crap, it’s limited to 100 transactions. oh, and they’ve disabled the online banking integration elements. shit. next.

iBank 4 - great a 30 day non-transaction limited demo. seems intuitive enough, handy tool to check out the supported financial institutions for direct access. looks like the interesting banks, brokerages, etc, are supported, sweet. start adding them. login failure, are you sure? what? wait a second here, seriously? try again, INBOX blinks. too many login failures? account locked? oh hell.

the balance of the options out there look like crap. i’m loathe to wade through that morass. best make one of these work.

update - 16-july, 2011

it’s worth pointing out that we did in fact settle upon iBank. i worked through a handful of the foibles that i had. its ability to interact directly with the bank in terms of getting transactions, etc. the trial leaves some of the annoying warning dialog boxes in play despite your request to not keep showing them in the future. this is addressed in the production paid-for version.

the process of getting all of your financial information from these systems and understanding your cost-basis, etc. is largely subject to the whims of your financial institution and their willingness to give you access to all of that information. jp morgan chase, you can bite me. 90 days of downloadable history is shamefully little history.

we’ve actually been able to get access to information via iBank that we couldn’t get via mint and this has proven to be a welcome addition. the iphone app is pretty cheesy. but it’s useful for periodically checking what you’re up to and manual transaction entry is handy. things are looking up on this front, not great, but not bad either.