I’ve written before about my problems managing my iTunes library and it’s just getting worse and worse so I’m posting again in hopes that someone has figured out a solution or something that can help make it a bit less sucky.

So here’s my problem, I have a huge iTunes library. Easily 100 gigs. My main computer is a laptop, which doesn’t have the HD space to hold 100 gigs of MP3s. Moving it to an external HD was my original solution except if for some reason iTunes was launched without the HD being plugged in (by clicking an iTunes link, plugging in my iPhone, or any number of other reasons) then iTunes would not see the external HD, redirect the music links to the internal music folder which of course didn’t contain anything and then break all the links. Upon plugging the HD back in, iTunes would not look at it and the songs would remain broken and would need to be fixed by hand one at a time, or reimported creating duplicates. Argh!

My follow up solution was to have my full library at home, and a separate library, much smaller and mostly newer, on my laptop. Occasionally I’d dump the new stuff on to the old larger library and keep fingers crossed that this synced. Well it never did and I’m back with two different libraries both with tons of duplicates and missing songs, even though the files are there.

This really sucks.