YetAnotherPotato

You've probably already looked this up, but here's a loooong youtube video by a guy who looks like he's gotten Oblivion Mod Manager, BOSS and Wrye Bash (I think, I didn't watch the whole thing) to run on his Mac using Wineskin. He installs Oscuro's overhaul during the video. I guess you could try getting OBMM running following his instructions and see if that helps. I'm lazy, so I just sacrificed some disk space to the Bootcamp gods and I now have a momentarily stable teetering pile of mods and am very happy.