Winamp crashes when syncing music library

[UnWarierMage224]

Hi all,

Winamp's being... temperamental, to say the least.
I have a music library of ~2000 songs which I want to get it to sync to my MP3 player. It recognizes that my player is connected to my PC just fine, but when I tell it to sync all 2000 songs in one shot the program freezes and crashes.
I really do NOT want to have to sit at my PC for hours and sync my music library 50 songs at a time. Is there a workaround for this problem or am I just going to have to bite the bullet?

Thanks,

-'Mage

EDIT: Mods, please delete this thread, I reposted it in "Misc. Software". Thanks.