That's a beautiful 5288, the 88 series were excellent designed tractors, I wish IH would have survived intact. Case got lucky to piggyback on some first class engineering.
You definitely have some nice, clean looking older equipment. I also have a 1086 and will be looking for a 2+2 in the near future. I'm trying to stay with non-computer tractors since I'll be farming only 100 acres I own until I can find some land to rent and I can't afford new tractors or their bills for repair work at the stealerships.
I can't understand why he would give your comment a love yet not answer your question, so I'll at least offer a good guess for you. Since he's wearing a St Louis Cardinals shirt, he's probably in either eastern Missouri or southern Illinois.