Okay, I still have problems with jEmplode under Mac OS X.
I also can't get USB to the empeg to work under Virtual PC. However, it does give it a college try, and it's possible that my slow Mac is keeping it from working properly. The Windows installation running under Virtual PC sees the Rio Car USB device properly, but it doesn't seem to be able to communicate quite right. A new/faster Mac might make it work better. Then again, it might not.
However, any new Mac you get is going to have an ethernet port on it, so even if you're not using it for a real network, you can spend $5 or so and get a crossover cable to get the empeg connected via ethernet. And emplode via ethernet under Virtual PC works just fine.
Virtual PC is also supposed to support a number of serial adapters, so you should be able to do serial upgrades, as well. That's all very standard, so I doubt you'd have any problem with that. However, I don't have any way to test it, so don't take my word for it.
Also, you could keep an old PC lying around but install Linux on it. The empeg guys have a supported tool to upgrade via Linux as well, and you might get more use out of a server than out of a random Windows PC stuck under a desk somewhere.
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Bitt Faulk