I've never used MS Money. I used Quicken for many years. The downloading and reports were great (and I won't take the time to enter everything manually, no matter what system I'm using) I was very unhappy with the way its budget tracking works. For example, I tend to go on a big clothing shopping spree twice a year, usually when the sales hit, but I don't necessarily know exactly which month -- one year it might be Jan and Aug, another it might be Feb and July. If I budget $600 for clothes in Jan, but spend it in Feb instead, it looks like I'm way under budget in Jan but way over budget in Feb. If I try to say I'll spend $600 for the quarter, then it insists my budget is really $200 each in Jan, Feb, and Mar.
I've switched to an envelope system (
Mvelopes) instead for budget tracking, and for the first time the tracking is actually influencing my spending. When I was using Quicken I would spend hours making cool reports, but it didn't actually impact how I spent my money.
Quicken looks nice for investments, and I am planning to upgrade and try tracking our stocks and mutual funds in it -- unless someone can tell me why they like MS Money better for investments. Or perhaps some online tools like Morningstar are better?