I have a similar situation, accept you are slightly older. I was born and raised in Annandale, but my Dad's side of the family has been in DC since the 1800s. He moved out of the city in the 70s (he grew up in Anacostia / Fairlawn). Anyway, I started hanging out and going to punk and hardcore shows in the early 90s (Chamber Of Sound, Asylum, old 930, old Black Cat, random church halls). I was taking the metro around town by myself or with a few friends at age 14/15/16, and the empty city felt like our playground. It was great, can't really say I ever felt unsafe. Outside of the 14th Street hookers, or maybe some eccentric homeless person rapping or singing for money it really wasn't that bad for us at all. Met a lot of good friends I still have today roaming around the city going to shows back then too. That's the old DC I miss.

I also use to spend summers (late 80s-early 90s) working with my Dad and his plumbing business. We would be at Atlantic Plumbing Supply by 630am which was usually filled with a group of colorful characters cracking jokes and carrying on...then off to job sites throughout the city by 8am...I can still smell the wharf in the hot summer air to this day. What a magical time.