crazy_dave: I've been somewhat successful at getting a lot of the non-DosBox/scummvm (which always seem to work equally well) working in WINE using wineskin. The only major issue that I've run into is that WINE-OSX doesn't support USB joysticks (though they say they do and WINE-Linux does) and USB HID devices in general are a bit finicky.
rampancy: Have you tried CrossOver Games? I haven't had any experience with joysticks, but I have successfully used gamepads with it.
As a Mac user, I still would get it here, if only because of the extras, and hey, it's GOG - if there's any gaming company which deserves my support, it's GOG.
Agreed about GOG. I haven't bought anything from the Mac App Store yet either, but I think I still might choose GOG if there was a choice. Apple gets enough money from me (and quite a lot of it for a long time I might add). :)
Unfortunately some gamepads and other HIDs do seem to work, but joysticks by and large don't. This is true regardless of engine. I've put in some of the CrossOver game engines into Wineskin (plus the CrossOVerGame engine didn't work well with a coupl of my games).
There is a bugzilla bug report for joystick support (and general USB HID support) in OSX
here. If you have USB HID devices that worked, leaving comments as to what worked with what games and what engines could prove really useful!
As a side not: thanks for the helpful tutorials you, NoanRand, and PalltheTall put up. I hadn't ever ported before and they were a great to help me get started. Finding out about Boxer through your GOGmix was great too. Wineskin is great (just put out a new release too).
In fact, soon I may have some games for you and NoanRand to add to your OSX compatibility GOGmixes. ;) Especially if joystick support gets added! I have Red Baron 3D and IL-2 working in all but the joystick. Red Baron 1 of course works, including the joystick, flawlessly in DosBox.
BTW ... do you have a 16:10 or 16:9 screen? Do you run the old 4:3 games stretched or with the original aspect ratio and black bars? Some games have ini files to manually set the screen for widescreen often without stretching, but not all the older titles seem to have that capability.