Elixirel: Did you manage to run it fullscreen on the Mac? Wine refuses to do so in my case, al I can do is window at screen resolution but that leaves the menu bar at the top. . .
Also, there is a minor issue with the x360 controller driver and Wine, it has very little dead zone so its easy to make mistakes.
Occasional frame rate stutter when running on Wine. Like all other games, it runs better natively.
In newer wine engines like 1.7.2 or 1.7.3 I have some issues in fullscreen, but with wine 1.5.31X and with Mac driver enabled in Wineskin screen options it is all ok.
Also you can set dead zones for xbox 360 controller directly in tattiebogle.net driver options in System Preferences pane