iTunes + iPod = lots of swearing

I guess it's more iTunes I'm having trouble with but I've only been cursing Apple since I bought an iPod.

We're told that they're so easy to use. What we're not told is just how finicky iTunes is and how happily it will erase whatever was previously on your iPod at the drop of a hat. For any person fortunate enough to have not bought one yet, learn from my mistakes.

Setup:
Most of my music (~14 of 16 gigs) is on an external drive since I don't have a lot of confidence in laptop hard drives.

I noticed that every time I plugged in my iPod, my computer would be pegged for about an hour and a half. Finally, I realized that unless you override the default setting and say that you'd like to manage your own collections, it will completely overwrite EVERYTHING on your iPod every time you make the mistake of plugging it in. Thanks Apple. I figured out that little problem and was briefly happy with everything working fine. Little did I realize that this was just the calm before the storm.

Problem

If you ever fire up iTunes and forget to connect your drive, you're basically screwed. As quick as a wink, it will zip through all your music and mark it as missing. Ok, fine. Plug your external drive in and... those songs are still missing?!? If you double click on them, iTunes cleverly realizes that it's made an error and it does actually exist. There doesn't seem to be any automated way to get them all back unless you click on each missing song. Given that I've got ~4000 songs in my collection, that could take a while. Grrrr.

Solution 1

I had noticed in the past that if I re-imported directories that I'd updated with new music, iTunes was actually smart enough to only import songs it didn't already know about. Perhaps, it's smart enough to find my missing files if I re-import my directories.

Nope.

Now I've just doubled the size of my supposed playlist, even though it can only find 1/2 the songs.

Solution 1b

Ok, so iTunes has this fun little feature where you can delete duplicate songs. Can I just delete the ones iTunes can't find? Don't kid yourself. I have the option of going through and selecting every other song in my freaking playlist and then deleting them (single clicking 4000 songs is slightly less painful than double clicking 4000 songs... after all, I'm saving about 4000 clicks...)
which almost seems palatable until I realized that playlists are associated with the MISSING versions of the exact same files I just imported. WTF??? Aren't they the same files? They live in the same place! *groan*

Solution 2

Hey, maybe I'll just delete everything and re-add them. Ok, that kinda worked except for my exceptionally short memory. I've got all my songs back but now all my playlists are empty. No problem, I'll just plug in my iPod and manually copy over all the songs in my playlist there (recall that I've set iTunes to manually sync with my iPod.) I happily plug in my iPod and ... hey! Why is it updating? I didn't tell it to do anything yet! Make it stop!!!!

Apparently, that setting was designed to lure me into a false sense of security. Now all my playlists on my iTunes and my iPod are empty.

Fuck you, Apple.