I haven't played with Money, but I've been using Quicken since the mid 90's. So far as I know, both support very similar features sets (of course, there's no "Money" on the Mac). The big difference is where you don't see it -- importing data from your bank, your credit card, etc. Both tools support OFX (open financial exchange), but Intuit will only download OFX from a whitelist of vendors who pay Intuit for the privilege and pass the cost onto the consumer. With Chase Bank, at least, it's costing me $6/month, although Fidelity gives me downloads for free. I'd be curious to know whether Chase charges less for downloads to Microsoft Money, which I understand doesn't do this sort of extortion with the banks.

Also, apparently, Intuit has been dorking with their file formats. If you hunt around on the web, you'll find that nobody imports data from Quicken 2005 yet, although I expect that Microsoft will catch up in that arena. In short, Intuit is doing everything they can to behave poorly and squeeze money out of everybody.

Ignoring those cost issues, the only real complaints I've got with Quicken are:

- not very helpful tax estimates for doing quarterly returns (and, Quicken 2005 helps you even less if try to use it in FY2006; you loose the unhelpful "wizards" and only get the "reports")

- poor handling of options trading (if you mess with puts or calls, then you're going to want something better to track them for you)

- no easy way to tie reimbursements to expenses being reimbursed (I'd really like to say "these five expenses were for the same trip... and this check is meant to reimburse that trip... and any under-reimbursement becomes a tax-deductable expense", but I pretty much have to do it all by hand)

At this point, I've been upgrading my Quicken every other year. The year-to-year changes are almost indistinguishable. I'd give Money some serious thought, but what I really should be doing is looking at something like Gnucash.