I would pick out a few guns in the price range that you mentioned, then I would go to the local gunshop and see which one fits you the best. If it was me looking for an auto that fits your needs (with good looks) it would be a Benelli Legacy. If it was an over under I would take a look at the CZ line of shotguns, Citoris, and Berettas. All would fit the bill nicely.

I currently shoot a sporting clays league (we are in the championship this week), and I shoot a Benelli M1 Super 90 with a 24" barrel and a camo stock, last week I shot 48 out of 50 with that gun. I am looking at buying a Benelli Legacy or some sort of O/U for a pretty gun to shoot/carry while guiding pheasant hunters and busting clays.

Another option would be the Ruger Red Label.

Well I also shoot sporting clays and bird hunt so I'm in the same boat as you. Autos are nice, but there are more moving parts so theres more of a chance for a mis-fire or a jam. I actually have an 1100 auto (ported, briley choke, etc...) and a Browning Lightning Sporting Clays O/U. I really like both of them so if I was you, just pick out a few different modelsand try them out. I was going to buy the BenelliSuper Sport instead of the Browning, but after doing research on them I found they have been having trouble with them cycling. Weight wise my 1100 and Browning aren't different enough to complain about. I would also recommend 30" barrels if you are a bigger guy, mine are only 28" and I wish they were longer.