Your answer would be it depends on a million things.Like the specific property, its condition, location to desirable areas, local STR regulations etc.We would need much more detail to be able to help.

Do a thorough market research and consult with local real estate professionals.Good luck!

@Quiana Berry   You need to look at the numbers and local legislation. 

Here some of my advice first Educate yourself Understand the local rental market trends, property values, and rental demand.

Let's try some local real estate meetup groups.

Talk to a local lender to know what you can afford.  2.Research how to do real estate transactions, get a good RE lawyer or find a good investment knowledgeable agent.

Does anyone know of any organizations/charities that offer rental assistance in Montgomery County, Maryland?

That region will require some risk mitigation, and would be better suited for a local flipper specializing in those types of properties vs buy and hold OOS IMO. 

I'd definitely double check and triple check your local/city regulations in regards to rentals, so there are no surprises as to what you can do legally. 

Definitely want to consult with a local realtor or real estate attorney