I have installed the concurrent version of emulators/i386-wine and so far Wine itself runs fine. I want to play the original Fallout via Wine and downloaded the current version from gog.com. Installation went fine, but at the end of the installation it throws some strange error codes, but nevertheless finishes "successfully".
When I then start the game it's launcher looks fine, but the game itself looks somewhat monochromatic / negative. Beside that it runs fine. I've discovered a config tool inside Fallouts installation directory and there you can switch graphics vendor from DirectX9 to DirectDraw 7 or "Basic". I've switched it to DirectDraw and then the graphics look fine and as intended.
Any idea why DirectX9 isn't working? According to winehq.org someone successfully tested Fallout with wine on FreeBSD 6 (!).
Last issue is that when I quit the game I get instantly logged out from X and/or X itself crashes. Could this be an issue with Xorg configuration and/or the driver. I have the current package of x11-drivers/xf86-video-intel installed.
Update: Yesterday I've installed the Lumina DE and here X isn't automatically logging me out after quitting a game via Wine - with XFCE the problem persists.
If you say you're not having that problem with Lumina, then probably XFCE is the problem. But in any case, I would not recommend emulators/i386-wine, as it is version 1.6 and therefore very old. Use emulators/i386-wine-devel instead. Also make sure you have your packages up to date, you might want to perform # pkg upgrade once in a while. I myself have no trouble with wine and KDE4, you might want to try that, too.