[on Fri 08 of Jan., 2010 10:52 EST, by rsbohn]
Seems like the bootloader trouble on Mac OS could be solved if there was some way to force the bootloader to remain active instead of launching an application. By this I mean that the board remains in dfuIDLE mode. Suppose the bootloader would check a pin, perhaps one on the extension port, and remain resident if that pin is grounded. I think this would allow you to flash the board from Mac OS.
Alternatively, if you could clear out the application in Flash it looks like the bootloader would go to an endless loop (main.c:165). If you can stand to run your programs from RAM every time that might work.
Do you need JTAG to re-install the bootloader, or is there some way to patch it?