Hi! eroge on the Mac OSX is such a niche segment of the game population...I've used Wineskin as well to "port" some eroge games to OSX, with different degrees of success...since I'm no expert @porting...
Haven't tried the classic Kanon, but just tried with "school days hq", and it seems to work ok...there's now an official patch on jastusa.com...haven't patched mine, but since I haven't gone thru the whole game, I can only say that it seems to work ok in windowed mode...don't like playing visual novels in full screen...some other games on top of my head that seem to work in Wineskin are: Dengeki Stryker, Harem Party, Bible Black, Go Go Nippon, Quartett!, etc...the ones that are hairy to get Wineskin to run are the 3D ones...Illusion games come to mind...most of the games have broken models, disjointed limbs...I've only seen a couple ones running with ok graphics, like Biko 3, Schoolmate 2, Des Blood 4, Real Girlfriend...
If you got a game working/ported, let us know here...how you did it...!
It'd be nice to have a list of playable eroge games on OSX via Wineskin, and how to get them running, if there are any extra steps...!
Cheers!