The (sad) tales of a 5th Gen 80Gb iPod classic

Question

Hey folks,
So here's my story: for years, I had a 10 Gb iPod. I bought it when the model had just come out, so you can do the math of how long ago that was. Over all years of using that iPod, I never ever had a single problem with it. I always used it on my Windows PC, no problems at all.
The story sadly changed when I bought my new 80Gb 5th Gen. iPod (which was bought a couple months before the touch models came out, so it's now a Classic - sorry, that part always entertains me).
Since buying that one, I've had a few problems I never experienced before. Songs that always played perfectly on my old iPod seemed to freeze the new one (I kept a copy of most songs on an external HD, so I could listen to them at work and so on, which made it easier to upload them to the new one). 99.9% of the songs came from CDs I own, and ripped through iTunes, mind you.
For that and other reasons, I had to learn quickly how to reboot my new iPod, something I'd never done on the old one.
And now, the greatest problem of all is here: since I installed iTunes 7.5 on my PC, it crashed a couple times while managing my iPod. Earlier today, after it happened for the last time, I recalled iTunes to notice that many of my songs on my iPod - HUNDRED, mind you - are now missing. As I go through the list of songs in my iPod, I get the "white exclamation mark inside the grey circle" next to the name of the songs. As I try to play them on iTunes, they don't play. As I try to play them on the iPod, it automatically skips to the next song.
No, I do not automatically sync my songs, which means there's no reason it should look for them again. They simply "disappeared" physically from my iPod apparently.
I called Apple about it. The first tech person was, with all due respect, useless. His suggestions were simply "reformat my computer" (???) and "reformat my iPod," but he gave me no explanation whatsoever for why (does "because my sheet says so" sound familiar?).
I finally got to talk to a supervisor, who did sound extremely more proficient and knowledgeable about what she was saying. In her opinion, for one reason or another (again, ???), my iPod lost the path to those songs. So, although they are physically in there, the iPod doesn't know anymore how to actually find them to play. Her suggestion, unfortunately, is also to reformat my iPod, and reupload all the songs. This, however, would not save any of the Playlists that took me forever to fine tune, as there is no way of saving Playlists from iPod they know.
I am officially scared right now that I will spend hours reformatting the iPod and reuploading the songs, just to have the iPod do the same thing again, to the same or other songs. The other option I can think of is to reupload just these "hundreds" of songs manually, but, again, what's to say it won't happen again?
In some ways, I do miss my trouble free older iPod.
Hope this helps someone who may be considering a change, or may be experiencing something similar. If you are, I'd appreciate some input on the matter!
Have a good one, folks,
D.

Answer 1

Just wanted to give you guys an update: my iPod now works again fully, without having reformatted it, as Apple suggested.
I was reading some other posts around here, and decided to try something before going for the ultimate/decimating solution: redownloaded iTunes and reinstalled it. Install of checking for updates, I just went to Apple's site, and downloaded the whole thing. Plugged in my iPod, and now it all works! All the songs that wouldn't play before are now working just fine, as before.
Seems to me there's something funky on iTunes 7.5 for Windows or the upgrade process, which wasn't there in previous versions.
Hope this helps!