I switched from Money to Quicken about 10 years ago, and it was a definite improvement at that time. However, the " will stop working on xx date so you have to buy the new version" is something Quicken does too. When it happened a few years ago they claimed it was due to the fact that banks had changed to a new protocol and the existing (2003 maybe) version wasn't compatible [of course they couldn't patch or upgrade those old versions]. So I was forced to upgrade to 2008 version, which was more cumbersome, with functionality modified. Now that I've gotten that version configured and am fully comfortable, I get the popup that the product is only good for 3 years and I need to upgrade to 2011 if I want to retain online capability.
What really annoys me about this is if they want an ongoing revenue stream, just make me pay for a license renewal and let me keep running the version I am comfortable with, instead I have to battle all the malarkey useless (to me) improvements that are added to the new version.
I tried Moneydance and after importing my data from quicken, would go online and then have duplicate transactions for my banking data. Also for some reason it couldn't connect to Mastercard account (Discover works fine) indicating that the password was wrong (I confirmed it was correct0) - this was a PITA because after two "failed" logins my credit card would disable the login and I'd have to call India to get it re-enabled.
I'll reluctantly upgrade Quicken, but overall I'm not a satisfied customer (read: given a viable alternative I'll abandon them ASAP).