I've been using personal finance software since Dollars & $ense on the Apple //e. Quicken and Money are really the worst examples of this type of software I've ever seen.
1. The more advanced any given feature on either of these pieces of crapware is, the more bugs it has. As mentioned by someone above, the UI for MS Money is
awful, awesomely so.
2. Quickbooks is better than Quicken, but it's still tied into a business model that does its best to get you hooked on a "subscription" basis for upgrading (the last I checked, which was a while ago).
3. GnuCash is an OSS alternative under development for Linux and Windows. (Works fine for me on Vista SP1 and Ubuntu 7.10.) It is still unfinished, but all features that a regular personal user would need are already functional. It has a very different way of looking at things than Money and Quicken. Absolutely everything is an account in GnuCash -- none of that "category" crap to confuse the issue. I love it. It still has a few rough edges, but it is better in its unfinished state than Money and Quicken are in their (ahem) "polished" state.
http://www.gnucash.org/
4. There's another new alternative called YNAB (You Need a Budget), which combines a budget system with some newly-added basic accounting capabilities for keeping track of account balances and such. Anyone looking into planning a budget and keeping track of simple accounts for personal use should take a look at this software. It has a solid and enthusiastic support forum, too. And the basic "rules" under which it has you develop a budget are an outstanding guide to maintaining a healthy cash flow and savings plan for your family.
http://www.youneedabudget.com/index.php
All other things being equal, and they usually aren't, the more advanced the accounting software, the more determined you will have to be to learn it and make it work for you. You have to "buy in" to the model your chosen software uses. Going half way with accounting software can be a recipe for disaster, unless you really know what you're doing.
Nothing is more frustrating than already-complicated software that is further complicated by huge numbers of functional faults and horrible design decisions. If you are in the least bit fastidious about the software you use, save your sanity and avoid Quicken and Money like the plagues they are.