Go to Iota early and have a nice meal (light fare or full meal at reasonable prices.) Say "hi" to Steve and I bet you'll get squired into the "music hall" when you're ready. If not, move up to the bar on the restaurant side, order a drink, and you'll hear some fine music; some of the bar seats also give you a view of the stage.
Parking garage on Fillmore is open late - unlike the one over by the movie theater off Clarendon Blvd. which closes a couple entrances early, leaving you to wander all the F**K over the place trying to find your car.
Virginia is not so scarey...See you there!