From my experience with the Sam & Max episodes the problems with running it in Linux with wine mainly come from the copy protection. (I can play the free version of Sam & Max 104 but not the free give away of Sam & Max 201) I'm hoping that I won't have too much trouble with my DVD version when it arrives.
So what about removing the copy protection and selling the games for Linux through a protected repository like: http://shop.canonical.com/index.php?cPath=19
I also remembered reading about winelib: http://www.winehq.org/winelib
Maybe this would help to make a version that works with Linux without too much work in porting them?
Just a couple ideas that were bugging me so hopefully now I've put them forward I can think of something else.