Not trying to persuade you either way but if you do move and try Wine for those applications it'd be much appreciated if you would update the Wine Application Database.
It's more that my customers are using it so I have to meet them half way. If I have a greenfield, I'll probably do it in tcl/tk or python/wx but I'm stick maintaining old win32 and winforms stuff for people.
My win32 stuff worked in wine about 7-8 years ago now which was nice.