Yeah, that's probably what's causing half the problem.
Here's what I was talking about in SyncMate:
Darwine? Nice.
I'd check it out if I wasn't running 10.6.3, there's no Snow Leopard compatibility. :/
I use
WineBottler, it's still in beta but it works. Slowly....
Also CrossOver, which is fairly neat. Let's you run anything in it's own little "bottle". The only issue is that you need to go through the process of bottling up each individual program. So it's a tad inefficient, especially if you have BootCamp or a PC laying around.
Best of luck!