When you say cool do you mean: full of cheesy people trying to hang out with other cheesy people? San Antonio is the home of the dive bar, trying to find anything else is futile. The only thing at 1604 and 281 is traffic.
I don't think people in SA can or want to pretend to be millionaires. No one buys it. Stonewerks crowd is preppy but doesn't feel at all like a 30k millionaire Dallas crowd (IMO).
i live in dallas. just happened to be in SA a few weeks ago and we ended up at stonewerks on a saturday evening. nice place. band was playing outside. not pretenious IMO, but then again i am in the middle of the 30k millionaires. it's SA, not the greatest singles town in the world, but i'd go back to stonewerks if i were in SA.
Chicago Bar at SW corner of Stone Oak/Huebner, nestled in the backside of that shopping center. It is basically a dive bar along the likes of the others that rule the rest of the city, except that it's newer and nicer. It's in the same center as the Cross-Eyed Seagull, and just a little ways down Huebner at the Blanco intersection is Kennedy's and a place called the Pointe. Take Blanco towards 1604 and you'll hit Stonewerks. Plenty of options very close, but I'd keep Chicago Bar at the top of the list.
I don't know about Sherlock's these days. More of an apartment crowd these days, more like $20K millionaires(read:ghetto).