Playlist Problems

I just bought a new macbook pro (I had a PC) and moved all my music to the new computer via music rescue. I reformatted my ipod so that I could update it with songs, etc. I got all my songs onto it without any problems, but when I play songs from a playlist (on the actual ipod), it will only say "1 of 5" and so on (instead of "1 of 78" or however many songs are actually in the playlist). Once I finish listening to the 5 songs or so, it will return to the home screen. So while it's not a huge problem, it's still annoying to only be able to listen to a couple songs at a time. Also, my computer only recognizes the ipod sometimes, usually after I put it into disk mode. I don't know if the two are related, or if I just missed something when I was changing everything around with the new computer. Oh, and I do have the newest version of itunes and ipod software, if that helps.