Switching from an ipod to an ipod nano and moving itunes

Question

The hard drive of my ipod recently died and I'm considering replacing it with an ipod nano and changing the computer on which my itunes resides. I have 3 questions:
1. Since I currently have about 4,000 songs on itunes, how easy is it to manage the songs that I carry on the ipod nano since the largest option carries about 1,000 songs?
2. How easy is it to move my itunes from 1 computer to another?
3. In moving the itunes to a new computer, will it make a difference whether some songs were bought via the itunes store and others were not (ie, copied from a CD onto my computer's hard drive using itunes)?

Answer 1

"Since I currently have about 4,000 songs on itunes, how easy is it to manage the songs that I carry on the ipod nano since the largest option carries about 1,000 songs?"
You can choose the update option "automatically update selected playlists only" which would mean you could create a playlist specifically for your iPod Nano and drag the tracks you want into it. If you tire of the list and want to change it, you just add or remove the songs you don't want. The ones you take out out remain in the library. Make your playlist a Smart playlist and limit the size to just below the advertised capacity of your Nano (around 1800 MB for a 4G). Or of course you can choose to "manually manage songs and playlists".
"2. How easy is it to move my itunes from 1 computer to another?"
Network the two computers and transfer your iTunes folder from one to another. I moved and iTunes folder recently between two Macs and for it quite strightforward. However as I don't use a PC here's a link that may help you out for moving on Windows.:
New PC & moving iTunes library
"will it make a difference whether some songs were bought via the itunes store and others were not (ie, copied from a CD onto my computer's hard drive using itunes)'
It won't make a difference in the move but you'll have to authorise the new PC to play the purchased ones. Don't forget by the way to deauthorise your old PC if you are disposing of it so you don't use up one of your 5 allowances: About iTunes Music Store Authorisation and Deauthorisation