The Roxio Media Manager that came with the pearl's desktop software is incredibly slow. Are there any alternatives, or am I stuck using it?

Just look at the Media card in My Computer. It should show as a removable drive. You can drag and drop files in and out of it.

That is way too easy.
Is there any way to make it connect like that with bluetooth? Mine will sync that way but it doesn't like to do file transfers for some reason.

You can send individual files by BT but not synch or drag and drop files. In the Media section on the phone, click Menu and Receive By Bluetoooth, then use your BT Manager on your PC to Send File by BT.

I also like using Media Monkey. Very powerful for tagging music files too.