Hi Bart,

Great article, and it's a topic that I'm very interested in myself as well. I've been a long time Quicken user, starting out with Windows, then I switched to the Mac version when I went Mac. (By the way, switching was UGLY - there is no direct file import between the two versions; you have to manually export all your accounts into their interchange format [QIF] and import them on the other side, and this is MESSY. When I did it I had all sorts of headaches - wrong balances, duplicate transactions, transactions that never appeared where they should have, etc. Maybe this was a sign of times to come that I should have paid attention to!)

Anyway Intuit's Mac support is lackluster to say the least. The latest version of Mac Quicken is 2007, and it's a PowerPC app. I'm not even sure it's Cocoa, it might be Carbon. It "sort of" works - well, it actually does work as far as "nuts and bolts" are concerned (i.e. it calculates my balances correctly), but has some minor but REALLY ANNOYING UI quirks (can't select certain buttons in certain dialogs, etc.)

But again, Intuit's Mac support is lackluster to say the least, and they have drawn fire and ire from the Mac community in the past for outright abandoning one their products (QuickBooks I believe). They've since started supporting it again, but for many (myself included) it's almost a case of "too little too late". Quicken 2010 has been out for Windows for a while now... I have yet to even see a "coming soon for the Mac" type announcement from them. And even if they do come out with one, I'm not sure I want to give them my hard earned money for it, given their lackluster history.

Anyway my major hangup has been support for downloading transactions from my banks. There are two ways that banks do this, one called "direct download" (where your computer connects directly with the bank's servers and speaks some sort of weird voodoo protocol) and one called "QIF" where basically you login to your bank's website, click some buttons, and it packages up your recent transactions using the Quicken QIF interchange file format.

Until recently there have only been a few that support QIF downloading (Cha-Ching is one of them I believe), and none to my knowledge that support the direct download protocol. Until recently. I have been evaluating Moneywell and was delighted to find that it supports direct download from both of my banks. Unfortunately I, like you, am having a real hard time wrapping my brain around the "buckets" metaphor. I kinda-sorta get it, but not really. So I've been evaluating Moneywell and have been (trying to) use it, but I'm still updating my Quicken data (so yes, every time I eat out or buy a newspaper or whatnot, I'm entering data in two separate places. Very tedious.)

However after reading through your review, I found iBank, which I hadn't heard about before for whatever reason. And when I visited their website, I was extremely pleased to find that they DO in fact support direct downloading from both of my banks, so I'll have to give that a look.

I'm curious as to see which program you eventually decide upon.

BTW, one quick note about Mint: your concern that you don't want your data there is (I think) a non-issue. They (the Mint people) use the same electronic clearinghouses that all banks and financial institutions use, so your data is "there" anyway. I also understand that they have some pretty heavy duty encryption, and good data compartmentalization and whatnot. And there is an iPhone app for Mint.