@Strom LeeIdeally you'd want to start by making a decision on whether you have the bandwidth AND desire to be active?

Option 1: getting out of this less desirable area with plenty of cash in hand to fund more deals right away.

Boston is a desirable travel destination, maybe you can factor in AirBNB for your multifamily and see if that makes the numbers work. 

My backup would be to refi & rent if needed as this is in a desirable part of town.

You can go down one street on the West side and be in a bad area and than two streets over is a well desired area.

(no "Home Base") My current plan is to look for a duplex/ split level that I could rent out one side and use the other as a permanent tax home while I'm on the road, which would also allow for an FHA loan as well.As investors, what do you look for in areas you don't live; such as how to find and what to look for in desirable rental markets, real estate agents, project management companies, etc.

The process would be to have an Architect put together a feasibility study to determine what can be built based upon the properties zoning and the desired use.

It happens to feed into a desirable set of schools which is  big attraction for working class families that cannot afford to live in Greenwood or some other A or B area.You mentioned your metrics include median home value and median rent.

@Kyle Starkey while VA loans may be less desirable to some, selling to a veteran may be appealing.

That is the most conservative number, the optimist number would be $440,000 per the comps. 15-20% under market value, and yes, not 30% under market value which would be more desirable.