I would lean towards Cleveland Park/Woodley Park/Van Ness in DC right on Red line Metro with restaurants, shops, grocery stores all within walking distance. Just my .10 cents (adjusted for inflation)
Posted By: Bengal Tiger
I'm close to your age and I've lived in north Arlington and downtown Silver Spring and while both are metro/walking friendly, both have a commercialized, yuppiefied suburban feel to them. One suburban area with plenty of local flavor is old town Alexandria.
If I didn't have to commute far away from the city, I would totally live in the city. Eastern Market is a great neighborhood, walkable, has local flavor and brick sidewalks and metro. The H street corridor is also great and being revitalized. the whole east side of the city is easily accessible for driving and has lower rents. If you're looking to buy as an investment, the east side is developing quickly. The northwest side of the city is also easily accessible by car but has much higher rents.
Adams Morgan and Columbia Heights have traditionally had a lot of unique flavor as well, especially if you like diversity. They are close to lots of bars, music venues, ethnic restaurants, and fun stuff. Living close to Rock Creek Park can be good if you like to get away from the concrete and tall buildings every now and then.
Other people here may know more about the LE situation in different areas. But if you're discreet and know your visitors it shouldn't be a problem. There are reputable local ladies operating everywhere here with no problems.
Good luck! I always like to see more lovely local ladies especially if available on weekends for incall.