Can't update ipod - not enough space but nothing is there

First, yes I have read the entire discussion a couple of threads down and it didn't help!
I have a new 2gb nano and am trying to load songs for the first time, using Windows XP. Every time I try to update, I get a message that it can't because there isn't enough space. I restored as suggested on a previous thread. I checked all my tracks and they are all 128. All my tracks are 3-4 mb. I do have more stuff in my library than would fit on my nano, but under options I have checked to only update playlists I specify and only update checked songs. I only checked one playlist and even went so far as to only check one song. So it won't even upload that. Showing 1.9g free space.
Any suggestions?
nano 2gb   Windows XP  

I think everything should be current. I downloaded the most recent iTunes yesterday when I got the ipod; Updater I just downloaded for the first time yesterday, as well as the ipod software. iTunes software is version 6.0.5.20 and ipod software is version 1.2. Yes, my preferences for only checked tracks and playlists, etc. were still there.
So I just now tried manually synching one playlist (the same one I was trying to do automatically before) and that worked fine. Which is some relief because now at least I have 70 songs instead of 0.
Subsequently decided to try out the new FM transmitter, which also worked fine, then came back thinking I would add some more manually. Now when I plug the ipod in, I get the message that the device can't be recognized. Tried the other USB port to no avail, same message. I know my port works because I run my printer off of it.
Arrrrgh!

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