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I was getting the same problem as remyabel in wineskin, so i tried the last version you sent him. It got a little further to "receiving incremental file list" till rsync crashed
I don't believe play on linux is an option for OSX users. And thankfully due to wineskin, wine is already compiled for us, or at least setup in such a way where it will compile easily if you follow the instructions.Thing is, there is a version of the game sold by G.O.G put in a wine wrapper. sstools5.1 worked fine. I don't think he'd want to leave anyone in the dust if he could help it.
SS2Tool will reject any game location under "Program Files" (or under the "Windows" folder for that matter), since these are restricted environments in which the game cannot function correctly. This seems to be the problem you're running into.
Hey, thanks for testing. Like previous SS2Tool versions it ends with the Triop chime (which one may not hear if speakers are off) and then self-closes. I did this because it's fast but if others find this confusing (please comment) I'll change it, no problem.