I very much appreciate your input. I thought there was something a bit "off" about him, myself... but couldn't even begin to pinpoint it. Saying that the "front and back end look like two entirely different horses" is a very accurate statement, IMO.
It's very humbling to me to realize I have 20 years experience in horses and know practically nothing about confirmation. ;-)
This was one of the most promising responses I got from my CL ad. The response came from a race TB breeder and stock agent... stating that one of their clients is looking for a new home (sounds like they'll be picky about where the horse goes, which I like) for this boy due to his lack of interest in racing. Seems like he probably was well taken care of. He's also sired by With Approval, which is pretty cool. :-) I may go take a look at him (and a number of other OTTB leads I have) in an upcoming weekend. It's about a 3.5 hour drive to get to where most of them are located.
Still... since they're going to be picky about where he goes, he isn't exactly in as bad of a position as most horses that come off the track.