All your sugestions are exactly what I did. And, if I had bought all my songs from iTMS, there would be no problem. The problem is the songs I didn’t buy from Apple.

Well, I do it everyday. There’s a folder called “iPod Control” (which is “conveniently” hidden by Finder.app), and there lies all musics. If they were properly tagged (idv3, or whatever they call it), they’ll come back in the same name. That’s a last resort, mind you.

Also, I store all music in another harddrive (via NFS, or USB), obviously in MP3 format. Buying music from iTunes is ridiculous, will never do that, and I recommend strongly against it. In this case, the iPod went into your way, not exactly OS X. Itunes came to the scene previously, and I was able to work with music nicely (with very few problems) since then.

Nowadays, I check out one or two podcasts from the list, and make up for a random playlist, and let it be. It’s impossible, anyway, for me to have an ipod that matches my growing collection.

The darwinports/fink thing is da bomb. Works almost like ubuntu (fink) or like freebsd’s ports (darwinports). Fink is about binaries, darwinports is more about gentooism.

Try something like Fink, DarwinPorts or install your things in /usr/local and set your user variables.

Another suggestion: when you backup your songs, backup the whole iTunes directory. You can overwrite it later without problems when restoring the system. About the iPod… if it isn’t paired with the current iTunes directory, when iTunes is asking ‘erase or sync’, open a Terminal, see where the iPod is mounted, go into this directory and copy your mp3 files (assuming that your ID3 tags are correct), but it is better to have iTunes directory backup.

“Why can’t I just use my iPod was a big USB drive and ask the computer to copy them from one side to the other?”

You can use your iPod as a big USB drive, but you can’t play from, let’s say, ‘drive partition’. :)
It is simple: it’s all about DRM.

It work fine for me, as we don’t have iTMS here in Brazil (as you know), and I don’t have an iPod (yet). I always heard that the “sync” is not a good option, as you can’t “sync” with two computers (and I have 3 here, 4th comming soon).

Also, on the “Apple crapness”, Aperture is a lot better for use than Lightroom (Adobe), but it misses two important features: easy printing (good for events), and speed.

Aperture is great for image quality, but is slow as hell.