Hi Vulcan.. your nick seems familiar... Do you remember me?
I have 55 gigs of music, about 14,000 songs. A "pain to do at first" is an understatement! With programs like shazam that listens to music and tells you what song it is, I don't know why iTunes doesn't have an option for it to listen to every song and correct the IDv3 data.
Just as AKHog said, I also amd totally anal about organizing my library of about 6800 songs. I do both windows file system, then manually use winamp to edit the IDv3 data to match spelling and everything. that way it transfers to everything properly.it is a pain to do at first, but if you are just starting a library it is easy to keep up as you go... get a song, do all the naming and ID before you even play it.
You guys must have a LOT of extra time on your hands.. I'm just glad if I have time to listen to music let alone start organizing it.Oh and iTunes is infamous for porking windows installations it can mess up your whole computer royally. Just FYI. Not something I'd ever install on my windows box. Luckily I have a macbook pro if I should ever need iTunes.
I'm interested in hearing more details about this if you have them - how exactly does it screw up the installation?