I use Microsoft Money 2003 to manage our finances. Overall, it takes awhile to figure out, but is a good piece of software if you are willing to spend the time with it.
I started using Quicken way back in 1999 - it came with the computer, but kept crashing for no reason. I had a free offer to try Microsoft Money, and since it didn't crash the computer, I stuck with it. I upgraded once to the 2003 edition, and had to re-enter a lot of information, so I have never tried upgrading again (the "if it ain't broke, don't fix it" mentality!).
The big benefits to using a program like this are the ability to keep track of due dates and get an overall view of the finances. I can't get some of the features to work for me (like the debt payoff calendar - it always makes assumptions that aren't true), and I manually enter things like credit card interest since the program never seems to get it right.
I also use it to track my income and expenses for a very simple business, and I haven't had any problems. It also updates our investment portfolio accurately, which is a nice feature.
Overall, if you are a very-detailed oriented person like myself, you can get Microsoft Money to do everything that you want, but it takes some work and is not very intuitive. I would recommend trying to get a trial version to see if it works for you before purchasing (downloads available from Microsoft website).