I forgot to answer what you ask about "how late can they play" again every show and venue varies. Some venues located in neighborhoods have an 11:00 PM curfew for sound level but when they are located in a downtown business area or in an isolated commercial business area they could go slightly later. Always call the venue during open hours to see if you can reach someone and ask. But my experience has always been the most shows end around 11 PM some slightly earlier and others that may go as late as 11:30 PM but I cannot remember specifically what time the shows usually end that I have been to at terminal west since I have only been there a few times. I'm guessing 11ish. Call them.

Actually, Most shows are stand only completely and visibility is good even from the back of the room, or the balcony, even for a sold out show they are good about leaving breathing room. Plenty of places to lean up against, However, my husband went to one that wasn't sold out (but nice full crowd) where they set up chairs from the front of the stage to about half way back to sound board...so my suggestion is the you call the venue and ask the layout plan for the particular show you might want to see.

You should have no problem arriving that early.