Is there a way to play the game on an actual window? Pressing cmd+enter just meks it a tiny, unmovable window on my 2nd monitor.

I found a setting for screen in wineskin, inside the contents, but i cant seem to figure it out. Any help would be appreciated.

I also tried looking for a cfg or ini file on the virtual C that the installation makes, with no success.

Ok, im making some progress.
On the screen options at wineskin, ive set it to run on a virtual desktop, which makes it into a window i can actually move around, but it's still stuck at a tiny, tiny 640*480 resolution. How can i stretch it?

The GOG Fallout 2 build has Sfall installed by default. Go into the game's directory and edit the ddraw.ini. You will want to change the graphics mode to 4 and enter a custom resolution into something more comfortable. If you disable the virtual desktop, mode 5 runs the game in windowed mode.
Maybe start with:
GraphicsWidth=1024
GraphicsHeight=768
You can also mess with the scaling methods and all of that if you feel comfortable messing with that.

Edit: It seems Sfall can cause issues with Wine. This mentions a workaround on Ubuntu. It should work similarly with the wineskin AFAIK.

i cannot find ddraw.ini, just a ddraw.dll. Where can i find it?

It should be in the same folder as ddraw.dll. On Windows it's listed simply as ddraw and is referred to as a "Configuration settings" type. Is it possible that OS X hides that file?

Hm, how would i go around showing hidden files on mac? This is all i see:

Taking a look at the screenshot, I can tell it wouldn't be hidden. Apparently, the Mac version doesn't use Sfall. That's why the ddraw.ini isn't present, along with a number of other files. You can try Sfall but as I said earlier, it can cause issues with Wine.

Unfortunately, I don't know of any way to scale the graphics to make it a larger window without Sfall. AFAIK, Wine doesn't support scaling the virtual desktop. Sorry I haven't been of much help.

well crap. I really wanted to kill time with this one at work.

Thanks for the help anyways!