[Wine] Gamemaker 5.3 under wine on OSX?

[jamdis]

I'm very new to wine, so please excuse my noobness.

I'm going to be teaching a course on Game Design for non-programmers in the fall.  The school is an all-mac operation, but I'd like to use YoYo Game's Gamemaker to teach the course.  YoYo has a mac version in beta, but it is unclear if it will reach release in time for my class to begin.

I know that the current version of Gamemaker doesn't fully function under Wine.  However, the AppDB shows that some people have had luck with version 5.3.  I can get this version to run quite nicely on my mac using Crossover Games, but it doesn't work with the current version of Wine offered with the Darwine Helper from Kronenberg's site.

I would love to support Codeweavers by having the school purchase CO Games, but the economic crisis has hit us pretty hard, and I don't think I can convince the school to go for it, especially since we will only need it until the release of Gamemaker for the Mac.

My question:  since Gamemaker 5.3 seems be able to run okay on linux boxes without CO games, and on my mac with CO games, is it possible that we could get it to run under a free version of Wine is just a matter of tweaking settings?  I'm willing to spend the time learning and experimenting with this, but if it's not likely to work I'd like to spend that time exploring other avenues.  Thanks in advance.