Everytime I use the Zune software, I try to play my music that has expired. It used to allow me to listen to them but they won't sync. But the bigger problem is that it asks me to re-install it EVERYTIME
When you say "expired" do you mean that your Zune Pass has expired? If that's the case then you either need to renew your subsciption or buy the songs.
I'm not quite sure what you mean by "it asks me to re-install it EVERYTIME". It asks you to reinstall the software? Are you getting any error messages?