And to return the original poster's question... Driving in D.C. really isn't all that bad, but if you're new to it and stressing out about it, your best bet is to purchase a ticket for the 9:30 Club's parking lot.
When I first started going to the club after I moved to this area in 1998, I parked in the 9:30 Club's lot. (I didn't know how to parallel-park then, though, so I guess street parking wouldn't really have been an option anyway.)
After the first year or two, I parked on the street. I've never had any problems, but I always make sure that there is nothing visible inside my car. (And I try to park on better-traveled streets rather than true side streets, although that's really more for my safety than my car's.)
The neighborhood where the club is located is also a LOT less sketchy now than it used to be.