Problems connecting to PC

I have a 20gb U2 Ipod. Recently I have been experiencing trouble with it connecting with windows. At times, my ipod freezes up while listening to music and I am forced to give it a soft reset (holding the menu and the center button). Then, I usually restore the ipod using Ipod updater. However last time, after I restored it, itunes would freeze after putting about 400/1000 songs on it. This was alright for a while because I didn't mind listening to those songs in the mean time until I figured out the problem. But last night, the songs on my Ipod decided they didn't want to play. I soft reset my ipod and attempted to connect it to my computer, which did not work. I got the "Do not disconnect" on my ipod, but it caused windows to freeze. I have now tried it many times and it is getting frustrating. Any ideas?