Welcome to BP @Algie Poole, great to have you here

If in at 337 sub2, lease option or owner-financed, easy entry without having to put new financing on it, you will increase your buyer pool significantly.  

From what I hear, the Somerville lotteries are much less competitive, so you're drawing against a smaller pool of applicants. 

I do handyman jobs like setting up inflatable swimming pools, installing window A/C units, and cleaning gutters.  

I am also looking to expand my network of real estate professionals, and am specifically in need of a great local handyman as well as a contractor.I hope to benefit from the vast pool of knowledge and experience here on BiggerPockets to support my own real estate investing as well as to continually improve the outstanding service and advice I provide my clients. 

We safely have about $20,000 pooled together that could afford a down payment on some of the houses we are looking at, and we would still have some reserve funds for a cushion should things go wrong after the purchase. 

It's 140 acres of mostly wooded rolling hills, two ponds (one spring fed), miles of trails, 1 Cabin  (1016 sqft, 2 Floors, 1 master bedroom loft, 1 bath), 1 Large 2 bay garage with carport, 450 sqft loft space with 1 bath and 3 queen size beds, in ground 20'x40' pool, 6 person hot tub and lake easement.

Having more duplexes will have to more liquid, get you into the residential financability, and also have a bigger pool of buyers if you need to get out.  

The profit is larger (of course more money is at risk), but I think your buyer pool will be larger with this option.

It's not impossible to fill a vacancy in December, but there will be a drastically smaller pool of applicants.