If you were a mac gamer at any point between 1996 and 2010, you have probably had at least one run in with WINE. Whether it is in the form of Crossover or Wineskin or Wine Bottler, we've all wanted to be able to play .exe files on our clearly superior machines (that was a joke please don't flame). It wasn't until I very suddenly got a SpyParty Beta invite that I seriously looked in to using it.
If your first thought after doing a little research is "Crossover looks simple", stop right there. Of the three options, Crossover is the only paid version that I would even consider, and given how poorly my experiences with the trial went, don't even bother.
That leaves Wineskin and Wine Bottler. Wineskin is typically my go-to application of WINE, but I have heard that Bottler has its uses. Installation of Wineskin is super simple.
First, go to this website.
Next, go to the download page and get the current version of Wineskin (2.5.8 at time of writing)
Load that sucker up, and you should see something a little like this.
I have some older versions of the wrapper too, but for the most part, I think you should just use the most recent wrapper available. I don't know what the AMD Speedhack means, and since I fear change, I've never tried it.
At this point, you should have a .exe downloaded that you want to run. Create a new wrapper using the newest version and give it a relevant title. It will be saved to a folder in C:...\users\yourname\applications\ which has very few real uses. I think that Steam dumps shortcuts there if you ask for one, but I never go to that folder.
Once that Wineskin wrapper has been compiled (it can take a few minutes), open it from that folder or from Launchpad and it should give you this window.
Click Install Software and then inspect the .exe. If it is a setup file, choose the first option, if it isn't, you need to make sure that the .exe is nested within a folder that contains only information related to that file. If the .exe is not a setup file AND didn't create a folder within downloads, you need to create a folder just for that .exe. Once you're done with that, I would recommend "Move a Folder Inside", just to keep the downloads folder clean.
Now is where we run in to some potential problems. Most of them should be resolvable by just reading the error messages it gives you very carefully (unless they are just numbered errors), but you might need to look something up on them crazy internets. The main problem I've run in to is a setup file not dumping the data to C:\Drive, which it needed to be.
I've had tons of games run flawlessly using Wineskin, and given how ridiculously free it is, I think it would be insane for any OSX gamer to not have it. The only disadvantage is that it can take a few minutes to create the files, but that is a hell of a lot faster then waiting for a port from a struggling indie.
Hope this helps and spreads the word about one of the best applications I've ever used.