Well, for starters a 2GB Nano will not hold 1000 songs unless you encode them at about 32kbps :lol: and that will just sound rubbish.
Most players (except mine

) have a 99 song limit in a folder which isn't to do with the space, but to do with how the player is made
If the player is reporting the wrong space (i.e less than the amount you are supposed to have) contact your seller and get a refund IMMEDIATELY
The AMV convert tool is for videos, which I assume is what you meant, so you will need Windows Media Player 10, The codec pack in the downloads and MP3 player tools 3.68
if you did mean music then there is no surprise that your stuff isnt being converted it is made for videos, I am not sure about the sound converter though (havent tried it) perhaps thats what you mean?