I am reading another comments and there are all valid arguments.
Let me put more options to include Into your analysis.
If you are planning to do development yourself , you need to know that condo conversions are most advanced project construction wise, as you a have to do full gut work with underpinning, building addition in the back and adding new uppper floor to maximize sqf. so if you are not into contruction world , your need to plan that your construction cost per sqf will be on the higher side.
Regarding waiting for 2 years or more , Zonning in DC is constantly changing, and it is constantly changing towards restricting development.
Before you could do a 3 condo conversion in most of neighborhoods and have high ceiling condo and roof access for roof deck as height limit was 40 feet for building.
Now it is 35 feet height limit , only two condos per unit , no roof access from inside the house and you can’t touch the front of the building.
That laws are mostly influenced by Historic Designations board and they are very active and influential in DC government.
If Trinidad becomes historic designated , not only that you will not be able to do your planned expansion , but they will control what kind of windows , entry door and fence you can put on your house.
Congrats on your purchase and good luck with your project.