I love Pittsburgh Winery for music. It's a great venue and wine is fun.
The wines are pretty good. They're all relatively softer in flavor. If your looking for a wine bar, Andy's or Allegheny Wine Mixer are your places. $30-40 for a bottle is a nice price.
The venue and music selections are where it is at. They seem to pick a lot of good bands. I seem to end up here monthly. The venue is fun. A nice mix of small tables, big tables, and standing room.
If parking is a concern, I typically always find street parking. You can bring food if you'd like. I occasionally see folks with food.