Almost all of my original media (CDs and LPs) for about 60% of my collection were lost in a fire several years ago.
Re-ripping isn't an option. RIAA says if I download a new copy, it is illegal and I have to buy new media, which RIAA claims is only a license to have one copy, which I already bought. Sort of like if I lost the title to my car I couldn't get a new title without buying a new car.
So fuck them. Just upload the music you have. If you bought more than 30% of it you're probably better than most.
While the above is atrocious legal advice, it's more likely than not going to be the norm. It's just sad that we're living in a time between the dark ages of zero digital media and the advent of a true digital media culture. It's patently obvious that we're going to have to get to the point that the average person can exist in a known legal state with respect to their media collection, but that's practically impossible today unless you single-source your media from a behemoth distributor who will stand behind you in court. That's not satisfactory.
My collection consists of a hodgepodge of tracks I ripped on Linux laptops at the dawn of cdparanoia from disks that have long since been lost during moves or destroyed, iTunes rips, iTunes purchases, Amazon MP3 free downloads, Amazon MP3 purchases, downloads from Jamendo and free online distributors and netlables, downloads from my musician friends of their own tracks, podcasts, and so on and so forth.
There is no practical way for me to "prove" that all of my music tracks are licensed for my use. It's simply an impossibility. Then we get into the legal grey area of ripping friends' CDs... the labels would love to claim that this is not legitimate, and that you must purchase the CDs in question... but that may or may not be defensible in court.
It gets even worse: legitimate bootlegs (e.g. of bands who allow recording); mashups; rips Web sources; recordings that include background music; and so forth.
In an ideal world, I'd say that we need the Federal Government to step in and provide a set of consumer- and artist- friendly media usage laws, but the problem is that the U.S. Congress is for sale, and most world governments follow U.S. lead with respect to media legislation (for the most part, but with notable exceptions).
Sigh.