Quicken 2010
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What was the problem? All of my Quicken import went through just fine when I went from 2006 to 2010.
That said, I hate a few things they did with the interface, but it's pretty much same old same old. I honestly have trouble seeing any reason to upgrade Quicken.
The problem wasn't the upgrade. I've been suffering with random accounts not updating for months. I think it was entropy. I finally put my foot down and decided to spend a bunch of time getting it all working.
Interesting. Using GNUCash, I always assumed Quicken actually worked and that it was just GNUcash that sucked.
Amusingly, my credit card supports OFX but my regional bank does not. Of course, GNUCash also helpfully informs me with a debug dialog when SSL certificates are valid. Since I've moved to putting all my daily transactions on my card (fraud insurance, interest free 30 day loan and cash back is a deal I've been going without for too long), OFX has made the process far less painful.
Quicken was great until I upgraded to 2010. I have had countless problems since then.
Quicken no longer offers phone support, only e-mail that answers half of the question.
Have you tried MoneyDance yet? http://www.moneydance.com/ A friend/co-worker (former Quicken/Mint user) swears by it, and it has all three of the important clients Windows/Mac/Linux.