Great ride! I used to ride much of that route when I lived in the area.
The Anacostia Trail system can be a bit curving and confusing (lots of forks in the road), so you'll need to pay attention. I would not ride those trails at night, however.
If you can find an alternate route than riding on Michigan Avenue, that would be a good idea. Traffic on Michigan is very fast. I've ridden on it but I was not comfortable, and I am an experienced urban cyclist. You can usually find an alternate route in the city.
The rest is fine. There are some hills after you cross the DC line up to Catholic U area.