After Hard Disk Crash...Upgraded to iOS4. Backed Up before...result?

Question

Fact:
1) Hard disk crashed
2) Replaced with a new and bigger drive
3) Installed iTunes
4) Connected my iPod Touch, clicked on Cancel on "Synced to another library...OK to erase message".
5) iTunes suggested upgrade to iOS4
6) Clicked OK on backup before upgrading
7) Upgrade result: OK
8) Selected Restore from Backup
9) All Apps OK, empty content. No music, no playlists, no movies, no podcasts.
Guess my mistake was, trusting that the backup before upgrading would work flawlessly. I do have a backup on an external hard drive, but is kind of old and is missing several iTunes purchased songs as well as movies.
Like many others, I had to try several times to get the backup/upgrade to work. When I click on "Restore from Backup" it gives me the option of Restoring from my iPod's name (you know the results) and one "unknown" backup. Should I try that one, just in case it has my library? Where can I look for that file in Windows? By the size, I'll know if that is the one that contains all my data.

Answer 1

What backup does is save your settings on your touch, not your Library. So I guess that was a basic misunderstanding on your part.
Backing up your Library would have been a good idea before you installed the new hard drive, but you do have the slightly older one available to you. You can transfer that library to your current hard drive, tell iTunes that the computer is authorized (new hard drive or OS install is perceived as a new computer) and synch your content back on. Applications you may have lost can be downloaded again at no charge. Sometimes the iTunes people will allow you to redownload lost music and videos.