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Most "add-ons", like schedules, roster packs or graphics, are available for Mac as well. Most of them are just files, not .exe files, so that shouldn't be a problem.
I can tell you my experience. When I got my Mac, I already had the Windows version of the game, so I used it in my Windows side. But, it was the only thing I used Windows for. I hated double-booting, so I have Parallels that I barely ever use. I recently got OOTP8 for Mac, and I love using it in the Mac environment instead of double-booting, so I'd recommend getting the Mac version. There are only three problems with the Mac version you should be aware of. First, you can't scroll with your mouse's scrollwheel if you have one. Second, you need internet access everytime you boot up the game (I leave it open in permanence, so I don't have that problem). Third, "foreign" characters such as éöîàç and so on are supported, but can be complicated to enter occasionally. To me, these are all minor disagreements compared to the huge advantage of being able to run in the OS X environment.
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