My iTunes library of music has finally got past the capacity of my 20GB iPod, and with me using podcasts now, can regularly increase in size by quite a bit. I'm used to being able to plug my iPod and any new music I've got will be put on it automatically without me having to do anything, but now it complains about there not being enough space. At the moment, I've gone through my library and unticked tracks I don't like so much and told iTunes to only updated checked songs on the iPod. However, there's no way of telling how many songs I'll need to uncheck if I get a new podcast or album that I want on my iPod, which still makes it quite awkward. How does everyone else deal with this? What is the best way of doing it?