I assumed the "(Bah ha ha ha ha)" after best OS would be enough to show it was a joke. If you didn't see it that way, it is.

Now, on to the fun questions...

All three of them can be answered with the following shallow statement. Windows is the most widely used desktop OS. In that respect, it is "the best." It also happens to be fairly simple to get hardware to interface with.

You get to do that without spending that $50, but you do have to invest in Mac OS X.
You seem to forget that Mac hardware (iPod included) is extremely overpriced. Even 68k Macs on eBay are too expensive for what they are.

But you didn't mention anything about Linux/FreeBSD/BeOS. On what did you spend $50 to get that to work?
Linux is only free if your time has no value. If you want to fart around with getting Linux to recognize the iPod, that's your prerogative. Same applies to FreeBSD.

BeOS is outdated and generally not free. I own the full versions of BeOS 4 and 5 and think that they had a LOT of potential. However, with only a handful of hardware (video cards especailly) supported, why bother?

Does it also enhance the iPod, making you need to reboot it once a day or crash?
As far as desktop stability is concerned (not server) Windows has been quite stable since NT 4. Windows2000 is even better than NT, and XP has yet to fail me.

Flame away...