di0nizus: All windows games I run with Wineskin Winery. I've been able to run most of them without problems. But as BoI: Rebirth here on GOG is windows only, I got no luck with any info on running it even on Linux because it's native on Steam.
Unfortunately I'm not familiar with OS X and Wineskin so can't really help you as how to configure it.. but as general steps to troubleshooting Wine:
* Locate the game logs. For TBoI they are located at "drive_c/users/USER/Documents/My Games/The Binding of Isaac Rebirth (Galaxy)" under the Wine wrapper you installed the game to. You should be able to find this information in Wineskin.
* Run the game from command line and look for errors. Again, the exact steps might vary, but essentially you set an environment variable WINEPREFIX to point to your Wine wrapper where you installed the game, and run "wine PATH-TO-GAME.exe" from the terminal.
* To debug Wine in detail, see
Wine Wiki (however, this can be too overwhelming and confusing) and try looking up any errors you find
* Reddit is a great resource to find others with similar issues. Try /r/macgaming or /r/wine_gaming for example.
However, since you mentioned you can't run it on Linux either it starts to sound more like a compability issue with hardware. If you can, you could also try running the game on different hardware. That's all I can think of.
It's really a shame when developers drop the support here on GOG and expect Wine to carry over.. especially when issues like these start to present themselves and there's not much the users can do.