Answer to question 1: you can, but it's not a simple drag and drop operation.
Here's a link to iLounge tutorials to show you how you can do this.
http://www.ilounge.com/index.php/articles/tutorials/
I avoid this by backing up my ENTIRE iTunes library. When I mean entire, I mean all of my music, video, and data information that is contained in the iTunes folder. (note: it also help to maintain everything in the iTunes folder; it makes recreating your iTunes library with playlists, ratings, etc so much easier).
I back up on a weekly basis to several different sources (NAS, external hard drive, and DVDs). I also back up every song I purchase when I purchase them, either through iTunes or another source (I like Amazon's mp3 downloads) to an external hard drive. It's redundant but it makes my life easier should my computer crash.
My old laptop recently died so I had to buy a new one. When I got my new computer all I had to do was install iTunes, move the new iTunes folder that was created with this new installation (I later deleted it), then move my iTunes folder that I backed up into the "my music" folder. Opened up iTunes and it was as if I was still on the old computer. Even my iPod(s) didn't know the difference.
Answer to question 2: Yes
Actually, I have more than several iPods. There are no limits to how many iPods you can put your purchased content on. You do have a 5 computer limit for purchased content, but that is for DRM'ed stuff only. iTunes is going DRM free for music and you would be able to put these purchased tracks on as many computers as you want. I don't think their entire music library is DRM free yet. Most of the videos (movies, tv shows) will still have DRM so the 5 computer limit would apply.
I have been avoiding the mp3 revolution for quite some time. I love my CDs and hate the idea of anything "compressed". But I also see what's going on around me and at some point have to pull the plug. I have had mp3 players before but with minimal memory. I am finally thinking of transferring everything to an ipod and have a question.
Let's say I have a collection of 500 CDs and put them all on my PC then on my ipod.
Question #1 - If my PC crashes, will I be able to take the ipod and xfer the music to a new PC if I get one?
Ok so now let's say I purchase a bunch of music for my ipod through itunes and then my ipod crashes and I have to get another.
Question #2 - Will I be able to get all those songs back from my pc/itunes account and put them on a newly purchased ipod?
Thanks! I am worried about these things and wanted to get answers before making the switch.

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