If you go with MoneyDance (I use and like the Windows version), here are a couple of resources for figuring out how to download data from banks that aren't on MD's list:
http://ofxblog.wordpress.com/about/
http://www.jongsma.org/gc/

To all terminally disorganized DCers:

Mark Forster (Do It Tomorrow/Get Everything Done; see DC's Forster interview: http://www.academicproductivity.com/blog/archives/24) is seeking beta testers for his new Autofocus system. I know little about it except that "One of the things I hope to get out of my new time management system is “autofocus”, that is to say the system itself will automatically focus on what is important and relevant to my life (and how I want it to be) without my having to spend time consciously sifting or selecting." His latest email indicates that it's a paper-based system, which means it's of less interest to me, but perhaps it will suit you and surely it can be modified for PC.

I'm skeptical about all these systems (except for their ability to make money) but will give it a look. The instructions will be revealed tomorrow, Jan. 5th. From Forster:

Please encourage your friends, family, colleagues, clients and anyone else you can think of to join this testing. I need a wide variety of people. It doesn't matter whether they think they are good at time management or hopeless at it. Nor does it matter if they think they won't have time to do it! I am just as interested in why some people don't succeed with it as I am in why others do succeed.

They can subscribe by going to my website markforster.net and entering their email addresses in the Newsletter Sign-up box in the right-hand margin.

It's true that you can use different machines with one license, but unless things have changed you need to get a new activation code each time you install, even if you've uninstalled from an old machine. This can be a bit of a pain, but I suppose it deters piracy.

I find several aspects of MLO awkward, including rearranging tasks (the implementation of drag and drop; keyboard shortcuts like Alt-Shift-Up/Down to move tasks instead of the more convenient Alt-Up/Down). I'm glad that others find the automated todo list useful, but I've found it unusable.

For simpler task lists I've reverted to tasktoy (http://www.tasktoy.com), which incorporates places/contexts, and taskthis (http://www.taskthis.darthapo.com).