The Oriole is definitely not hipper than anything. It's a den of debauchery for people who apparently need to drink at 6 and 7am which isn't cool whichever side of the day you're on. I've seen girls eating...well other girls there, bartenders sharing lines with patrons(their friends, it's a locals only bar), people sleeping on the floor, etc. It's a real cornucopia of hip things.
The pool was at my first place, just FYI, a place I rented downtown on Simonton. In no way was that pool mine but it was in ground and 4 ft outside of my pool house, where I lived with no kitchen, a shower and a bed. I did wax a few tourist chicks in there and oddly enough, two different ones named Mackenzie which I thought was pretty random(that was the actual 1 upper strokin').