BostonBanker: Your boy is gorgeous!
I've always ridden bareback; as Fuzz got older, we kept going to less and less tack. We'd mosey down the road with no saddle and just a bosal or his jumping hackamore (I probably could have ridden him with a halter and done just as well.) Something to be said for being partners for nearly 23 years...
Chance, on the other hand, is a firecracker! I have ridden him bareback in the paddock and he's done okay, but get him in the wide open spaces and all he wants to do is run. Him I ride with a saddle and the only one that fits him well is my dressage saddle (I've got a nice collection of saddles - western, hunt, dressage, McClellan and one of these days, I'd love to try sidesaddle.)