Several years ago, I switched from Quicken to MS Money for managing my finances. The two programs were virtually identical, and I think I had a free offer or something for Money, so the choice was pretty easy. And for a long time, I was fairly satisfied with what I got.
Lately, though, I have started to be more and more frustrated with the program. The major issue is one of performance. Upon launching Money, the CPU will peg at 100% for minutes at a time, when it seems to be doing nothing. Downloading transactions can take 15 minutes to a half hour, with the added frustration that it will sit there and do nothing until I go to enter a transaction, and then, only then, will it start "updating transactions" and lock the form I'm working on ("operation could not be completed at this time") until it gets to a stopping point. It's like it's deliberately wasting my time. When it downloads a transaction that matches a scheduled bill, quite often it will match the downloaded copy to the next instance of the bill (instead of the instance on the exact same date). If I'm not careful, it will consider that next bill paid, and I won't get reminded when it is due. And when I click "Change" to match it to the correct date's instance, it's another 5-minute-or-so wait before it shows me the list of transactions to match.
The straw that has broken the camel's back, however, is this new feature they've been trying to push for a while. The gimmick is, you link your Money file to a Passport ID, and you can access your financials from anywhere with a web browser. Sounds neat, but it doesn't take a genius to figure out this means uploading your information to Microsoft's servers. Call me paranoid, but I don't want my bank accounts on a publicly-accessible server that can be accessed from anywhere with a web browser.
It started with simple "reminders" that you can secure your data file with a password -- a move which automatically enables the "access anywhere" feature. However, now they have locked out one of the main features behind this "requirement". For some reason, the link to the online services for one of my credit cards disappeared, meaning I couldn't download transactions for it anymore. When I went to set it up again, Money insisted -- nay, required -- that I enable the Passport link. It also does this for new accounts, even new accounts at existing institutions. For example, it refuses to acknowledge the new savings account I just opened up, even though I'm sure it's already downloading it with all the other accounts from that same bank with the same login; certain, because before it decided to play this little "give me all your data or I start taking away features" game, I had opened new accounts at existing banks, and the very next update, Money offered to set up the new account it found. Not anymore, though.
Probably the most insulting chapter of this story is that it did not happen when I upgraded versions. It is the same Money 2006 I've had for over the past year. At some point, it must've downloaded a program update that took away a feature of the program that I use, and held it hostage in trade for uploading my account information to their servers.
And to think I used to joke about Microsoft requiring your bank account information before their software would work.
I don't know if the open source projects are mature enough for my needs yet -- they weren't the last time I checked, but that was a few years ago. I have a feeling I'll be purchasing a copy of Quicken in my immediate future.