As Gold my success rate for upgrades has been excellent. Always have gotten an upgrade to the executive floor at Hilton, with some both executive floor and suite upgrade. I also stay at a large Hampton Inn on Long Island and most of the time they upgrade me to a 1 bedroom suite. I suppose it helps they know me there and I stay fairly often.

I must say one's attitude at the front desk can go a long way towards upgrades and extras. A friendly, professional, kind, and appreciative attitude can go a long way with front desk/check-in staff. An entitled, demanding attitude rarely does, I have observed.