I've always been partial to Intuit's Quicken, even if the company hasn't always been particularly Mac friendly (although that may not be an issue for you).

Quicken is easy to set up, easy to use and easy to maintain. Set up the spending categories and you can easily surprise yourself at the end of the year. How much did you spend on eating out? Gas? Groceries? Quicken can help you find out.

This is not an evenhanded recommendation though. I haven't used other programs. I dabbled around with Moneydance but not enough to know if it was good or better than Quicken. I'm set in my ways I suppose.

Bottom line, Quicken is a pretty good option IMHO.

I had tremendous problems with Quicken's inability to import (or at least import accurately and painlessly) years of Quicken data from Windows, when I switched to the Mac about three years ago. I tried Moneydance, it imported every transaction effortlessly, and I've never looked back.

Tech support has been swift and helpful, exactly the opposite of Intuit's. Upgrades are free and painless--again, exactly the opposite of Intuit. And the Moneydance people seem, to borrow a phrase from third grade, very nice--again, the opposite, at least these days, at least for Mac users--the opposite of Intuit.

Moneydance could handle investments a little more deftly, but it's adequate for that use and on par with or exceeding Quicken with standard things like checkbook management and expense-bucket tracking.

My girlfriend uses Moneydance on her iBook, and she likes how all of her accounts show up at once, on the first screen. Then if she wants more info on one account, just click on it and there you go.

i’ve tried them all. quicken is the only one that reliably gets data for you (unless you like logging in to 5 different accounts every week, manually downloading .qfx files, and importing them) and does useful things with it. iBank is pretty and had the potential to be great, but it’s horribly slow (graphs can take 3 minutes to generate vs. quicken does it instantly) and limited (parent categories don’t show the sum values of subcategories…things like that).

i wish i didn’t have to recommend running an ugly monster like quicken for PC under virtualized XP, but if you are seriously looking for a good solution, it’s really the only option. the others are just far too frustrating and limited for multiple accounts, investments, planning, etc.