There are a few problems with this, including the fact that WINE is not guaranteed to be forward-compatible. Start with the newest version and go backwards, and you may eventually find one that does a good job of it.
I've kept away from WINE for ages though.
When it comes to VMWare you may have some luck with that, however only the 'vmware player' (I think it is) will have any kind of support for 3d acceleration. Without that you'll either probably get a slideshow when complex 3d elements are present. Periscope on subs, or a lot of places on the ffg and air platforms. (Or if it blacks out completely, it will be unplayable, since most of the interfaces are using 3d functionality anyway.)
Right now, I'm migrating all my "non-gaming" to a linux box, but my 'powerbox' is still running windows for gaming purposes.
I think I can avoid ever running Vista this way.
(Now, if I can only get hardware that isn't price-elevated and crippled for the sake of AACS compliance, I'll be a happy camper. And if games don't require 'higher than xp'.)