There was American Idol Reject in early 2009 which was put up for free. He also put out Tireshops & Night Clubs late last year. That one he was selling, but I believe he put up a download of it missing a track or two around Christmas as a "Christmas present." There's also one from a few years back called "U Ain't Heard" from 2005 I believe. He's also supposed to be putting out another "free album" this summer.
As for him signing, all signs definitely look to be pointing that direction. He's working on more and more Strange albums, and there's what LDS said (he's on tour, hyping for Krizz). I say go for it, with a little grooming, he could really go somewhere.
Craig Smith is another that may be on their radar, seeing as he's been on quite a few albums too (Sickology, The Lost Scripts, Raw & Un-Kutt, Gates Mixed Plate). I'd definitely say those are the two locals they're probably looking at these days.