iPod Freezes when Syncing Podcasts

Every time I connect my iPod to my mac it syncs the library, then goes to the podcast directory and freezes on about the third or fourth podcast. iTunes freezes when it says "Updating Songs on iPod ... Copying 4 of 20:..." and the iPod freezes on the "Do not disconnect" screen.
I am currently using iTunes 5.0.1 with Tiger, but I had the problem in previous versions of iTunes and before I upgraded to Tiger.
I went through the complete uninstall/repair discs/repair permissions/etc. twice and it didn't work. PLEASE HELP!!