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!

My hope is to begin building my portfolio (probably fix/flips) this year while I continue to work with local investors on helping them build theirs.

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

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.

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 

I don't have any local meetups but there are a lot of online groups.

I would love to get some advice from locals or any real estate expert with experience in Maryland on the best locations (cities, neighborhoods, etc) to buy this type of property at a fair price.Thanks in advance!