Here's the deal on our product. It *is* basically a commercialized version of Wine, and our Wine is, oh, 95% the same as free Wine. We make some tweaks here and there to make sure that our supported applications (like Office 2010, etc.) continue to work, even if they are currently broken in free Wine (which can happen from time to time.) Our licenses run from $39 to $59, which I don't know if I'd describe as "horribly" expensive... to me, paying $600 for Photoshop is more on the "horrible" end of the spectrum, but to each his/her own. Anyway, if you have the technical moxie to install and configure free Wine to your liking, by all means do so. On the flip, if you like a nice UI, with easy setup and install tools--not to mention having support forums, as well as technical support folks that will actually answer your specific support issues--then CrossOver may be a better bet. Be aware, too, that when you purchase CrossOver, you are *also* supporting free Wine, because we give *all* of our Wine patches back to the Wine Project. That's significant, because CodeWeavers' employees do a lot of the heavy lifting in Wine. So, if supporting Wine's development is personally important to you, sending CodeWeavers a little of your hard-earned money is a nice way for you to directly roll the ball forward. After all, Wine developers have to eat, too.
Thanks for your interest.
Very Best Wishes,