I know the sub 4% rate is attractive for multiple reasons but the Covid golden handcuffs are a problem for a lot of people.

All strongly appeciating neighborhoods, but can be a rough tenant base.A rent by the room situation (renting our basement if it is legal living space) could be a good solution in Brightwood or Riggs Park...or even Silver Spring.

I have had multiple roofers say that insurance will replace the whole roof due to that damage.

The HELOC would need to go off your personal situation but if needed you may be able to do DSCR on the short term rental.

Most Mortgage Banks have the ability to broker some loans and attempt to call themselves Brokers now as consumers are getting smarter and starting to realize in most situations Brokers have better rates.

You are best speaking with an attorney about this , I am not , and taking the attorneys specific advice for your unique situation in the state that you are in . 

You need to compare your cost of living, and overall personal cashflow each money with your current situation vs. this potential new acquisition.

Multiple train stops.

But I would love multiple feedback, constructive criticism, and differing opinions.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.