You can run JEmplode on Windows, so give it a try. It's got most of the stuff you'll need.

Even if you do find that JEmplode is adequate for your needs, be sure to get a copy of VPC anyway - it'll be invaluable if you're switching from Windows and don't want to keep a second computer around just to run odd programs.

USB support under VPC is fairly stable, but sometimes can be a little flaky. It is usually resolved by unplugging the peripheral, putting the VPC to sleep, waking it up and reconnecting. Since I sometimes have similar problems with Win2000, I'm not entirely convinced that VPC is to blame for this. YMMV and you're better off with Ethernet anyway.

For serial connections to upgrade the player and so on, get a Keyspan USB-serial adapter. So far this is the only manufacturer (that I know of) that has released OS X drivers. It should work fine with VPC.