Based on my experience with Quicken, your best bet is take a deep breath, yell "Shoot!" (or other expletive of your desire) and buy an upgrade.

I had a round with Quicken in the upgrade to XP.  It worked flawlesly ... except it would not print my reports I needed to give the accountant. And I of course discovered this at an inopportune moment.  (I'm one of those folks who are going to quit procrastinating tomorrow.) I finally gave in, bought the upgrade, imported my data, and everything worked beautifully.

I sometimes wonder if Microsoft doesn't own Intuit as well.