Reply to iTunes DRM Purchase Before 2009. iTunes Match?

Hi All,

I've got quite a bit of music I purchased before iTunes started DRM free stuff. If I join iTunes match will I be able to upload that music to my account and then download DRM free versions? Right now if I try to load this music into tracktor, I get the blinking red bar at the bottom.

Do I actually have to "upload" this music to iTunes or do they know it's in my account as a purchase?

Do I have to upload *ALL* of the music to iTunes Match or can I just upload the stuff I want? I have a lot of random files of tracks I've produced - so no need to send those online to get analyzed - iTunes won't recognize my unreleased demos!

All of my music was purchased legally!

Fores