I’ve been a real estate investor since Moby Dick was a minnow, and I've been satisfied with the 7K supplement to my military retirement.

The real problem is is I have no defined goal do I keep and let this little house supplement my income in my later years, cash out,invest elsewhere.

While you are occupying the property your mortgage is being supplemented by the income income from the other units even though you are not cash flowing you are making money as a form of savings .

Please don't try to use generic forms from the internet for Massachusetts. 

@Jared TownsendThanks - with the $100K liability coverage limit, why not supplement that with an umbrella policy?

See your loan documents for specifics -  this is a generic example.There is *PLENTY* of "velocity" to it.

All they would do is a generic POF letter. 

I want to own property that brings in some cash flow that will supplement my current W2 job with the goal of retiring early.  

My rough plan is to try and find something that works with an FHA 203k loan, preferably mostly cosmetic work as I want have more experience with rehabs before diving into a major project (probably a pretty generic / popular formula, which I expect is why I don't see many options that fit these criteria). 

A lot of the generic ‘is the house available’ and requesting to schedule a showing.