I’ve been able to calculate all my monthly operating expenses, lowest possible rent, and upgrades.

Electric heat can be very expensive in the winter so I would always encourage landlords to have tenants pay utilities so they have some incentive to conserve.

Since you’ll be saving your own living expenses by living in one of the units as required by the VA (to the best of my knowledge.) pretend you are paying rent and it should make your numbers look much better. 

This home has been highly operational with high rates of occupancy, bringing in anywhere from $500-$1500 a month in overage beyond our monthly expenses.

Ensure you account for expenses like maintenance, vacancy, or capital expenditures.

Costs include a conversion fee, potential property upgrades, and legal expenses.

MA is so so expensive I'm pretty much completely priced out of any areas that make sense.

It shows me the average price of booked vs unbooked properties from my completion that I can choose.

Should I live in this house after and buy more property with the 100k or rent it out move and try to buy more property, the only problem is my area is so expensive a new mortgage would be more then what im paying now.

Since you estimate a resale value of $200-215K and renovation costs of $60-70K (although you said that's on the higher end), your margin is tight, especially considering closing costs, realtor fees, and unexpected expenses.