Using the player with a Mac and Jemplode should be fine in the long term. The only tricky part is upgrading the player firmware.

You'll only need to a player firmware upgrade once in a while, so there's nothing wrong with using a friend's PC to do the job. Make sure to use the PC to both install the 2.0 Beta 11 software as well as the latest Hijack. Then future Hijack upgrades will be do-able with Jemplode on the Mac.

I guess it's possible to somehow upgrade the player firmware by using Windows emulation software on the Mac combined with some kind of a serial port adapter. I think others may have been able to do this successfully. If anyone's got a procedure for it, I'd love it if they could do a writeup here. But unless someone's got a step-by-step guide and/or you're willing to experiment with it, then the friend-with-a-PC is the most painless path to a firmware upgrade.