My other option to house hack is Pittsburgh as I have family there but the property taxes are insane and it seems like the room rental market is very college oriented (I could be wrong.)I'd appreciate any feedback on Hagerstown and househacking. 

The issue you may also run into is from a tax perspective, but I am not the expert on that.This seems too complex honestly and one of those, you cannot figure out what could go wrong until its too late scenarios.

@Carlo D.We have a separate account for both maintenance, as well as escrows for taxes and security deposits.  

I'd prefer newer builds with all the amenities and well run building.

@Richie Thomas most builders won’t sell to investors and cash flow would be minimal if at all for new builds.

I have lost $ 200,00 on the 3rd deal because they pulled the plug on that deal at the last minute without ever inform the investor to pivot to another deal. 1031 exchange rules are very strict so I had to pay the capital gains tax.

There are companies that do this for you and charge a fee, but usually it's for larger buildings. 

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

I am new to real estate investing but am interested in fix and flip projects and building a rental portfolio.

Also thinking of buying a single family and then flipping it to a developer to tear down and build new multi-family that seems to be going up everywhere.Any advice is appreciated!