I am on UNSTABLE, and I have i386-wine-2.0.1,1 with playonbsd-4.2.10_1. I tried installing i386-wine-staging, and it wants to uninstall playonbsd.
I have had fits with the couple of apps I have tried to install. I tried to install the Kindle app, which seems to be broken (the latest version is listed as bronze on winehq). I tried installing this both in playonbsd and on straight wine. I would get the Kindle splash screen then nothing.
Note that I have had both Starcraft and Starcraft II WoL working on linux.
I then tried to install Starcraft II Wings of Liberty, and that failed as well. Again, it iinstalled, but the game crashes as soon as it starts.
Since part of my problem is the way FreeBSD mounts (or doesn't mount) DVDs, I'm going to try the original Starcraft just as a point of comparison.