Hello I just wanted say that the GOG version of PST runs here on the latest crossover games and OSX Snow Leopard.
Do following
a) Install the game directly over crossover (in a winxp bottle)
b) Once it is installed go to manage bottles and then
System Settings -> Wine Configuration -> Graphics -> Set "Emulate Virtual Desktop" to on

That should be it, PST now runs in a Windowed Mode

I assume the same applies to Wine but I can only confirm it for crossover 10.1 here

Maybe this is a stupid question but is there any way to make the window bigger? I got the game to work but it's pretty small...

EDIT: Figured out how to save :p

I lowered my monitor resolution to 800x600 and that seems to work...a bit of a pain, but still!

There are high res patches which make the visible area bigger but everything stays small, i ended up to zoom in dynamically via ctrl mousewheel up on the mac (better than to reduce the overall resolution because it can be one quicker)
The game unfortunatly is simply fixed to a certain resolution.