We are currently living just south of Boston and are looking to purchase a 2-4 unit property in which we would live in one of the units.

But with that purchase, I bought it with $50k equity in the deal.

Mortgage lenders will qualify you for a higher purchase amount for multis than they would on a single, because they will count the rent you will be making on the other units as additional qualifying income for your loan application.

That 36% rent increase while keeping happy tenants shows how smart and intentional you are about building relationships, not just cash flow. 

We were in a financial position where we could keep our existing home, upgrade, and purchase another home.

However, a multifamily purchase could work quite nicely. 

I've got a property under contractPurchase price $78K out the door (I have cash to close) Intent: build on the property which already has a functioning well, septic, and needs PGE installed Total buildout on the property utilities: $128K including the original land purchase price.

Encore, you would need a membership, if you purchase in the new phase (Spectrum ) they automatically come with the amenities (membership) included to your guests, but the HOA and management have other restrictions and all units come furnished with the same packages, so you can't make changes to have it stand out, which is what is really needed hear in Orlando since there is so much competition. 

I only purchase direct from owner and no assignments.

I agree that is will be a gamble as to how well it will do.Also, ask the owner if they will entertain partial owner financing to keep from dragging family and friends into this risky business venture.Maybe even rent from owner for a year with right to sublease to see how it goes before committing to a purchase.