IPodTouch to 2.0 questions

I had a few questions regarding upgrading my iPod 32GB with 1.1.4 software to the latest 2.0 software.
I recently manually added 25GB of music to my iPodTouch and 2 700MB Movies as well.
I have two computers I use primarily and for home tasks and high end work related tasks; if i get the 2.0 software on Machine 1; will I be able to...if need be restore it if im using Machine 2 or have to reinstall either of my OS?
(i use XP and Leopard specifically)
Perhaps there is a way to save the file to my computer?
Also second question is, i notice alot of discussions about the newest 2.0 software conflicting with some songs?
I know more users post vocally about issues instead of stuff that is working...but is there anyone recently that has had it work successfully?
I have not updated or changed or did anything to my iPodTouch since i purchased it two months ago.
thanks in advanced.

There's a few issues to think about. First, I would say that unless you really want apps and games and microsoft exchange email, you shouldn't upgrade to 2.0 (which is now 2.1 anyway) until Apple issues some sort of fix for all the problems going on. There have been way too many people with problems after the upgrade. If you do upgrade, just be prepared for a whole host of issues that can pop up. Some people have been lucky, but I wouldn't count on it.
Next, the software load that is on the ipod has nothing to do with the version of itunes or the OS you're using. The only real exception being that if you're still on itunes 6.x, it will tell you to upgrade itunes first, so it doesn't really matter. What does matter is whether you sync with itunes or manually manage. My guess is that you manually manage since you're talking about using two different computers with the same ipod. If you sync, just realize that everytime you use a different computer it's going to wipe your ipod clean and resync. So bottom line, if you use one computer at home and another on the road, I suggest either manually manage your music or have both itunes libraries on both computers set up identically.
Lastly, if you finally decide to upgrade the ipod to another software version, you need to do it on the computer that your ipod is registered to. Otherwise itunes will wipe it clean of all music and reregister it to the computer you performed the upgrade on. So, if you're traveling and decide you want to upgrade in your hotel room with your laptop but the ipod is registered to the home computer, be prepared to lose all your music. Again this can be overcome by having all your music on the laptop as well.
I have experienced a lot of what you're asking about because my primary computer is a Windows Vista 64-bit system and itunes didn't used to support iTouches on 64-bit systems. So I had to use my old computer to manage the iTouch. After itunes finally supported 64-bit, I was using both computers for a while until I was able to get all of my music onto one computer.
Sorry this was so long. Hopefully it answered some of your questions.

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