I am using Musicmatch and having trouble manually transfering (rather than sync'ing) songs to my ipod. Transfering seems relatively straightforward by for some reason is not working. Any suggestions are much appreciated.

Your going to hear this a lot: Get Ephpod or Media Center 9 and ditch MusicMatch. You'll be so much happier with either choice. Ephpod is free, Media Center 9 is $40.

Use Ephpod. I use it to manually transfer all my songs and it works great. I never even bothered installing mmjb.