The on post housing is not that good which drives a lot of the soldiers to off post rentals.

Happy to share my experience:I was looking to diversify geographically, and though maybe a small ($100K) property might be a good way to test drive Roofstock.

Should I improve the property and use as a proof of concept to see if my market can handle a higher rent factor?

@Marielle Walter as stated above, Boston and the closely surrounding areas are VERY competitive right now - $5-600k will be tough (factor in your renovations after purchasing too). 

Driving for dollars is the best way to find properties 

Are there other factors we need to consider?

By Comps or by putting in successive prices for the properties until the analysis s give me the monthly cash flow and Cash On Cash Return I want OR have a RE Assessor do a drive by assessment?

Thus, the Department believes that in appropriate circumstances, owners and managers may develop and implement reasonable occupancy requirements based on factors such as the number and size of sleeping areas or bedrooms and the overall size of the dwelling unit.

That will determine your CapEx exposure, which drives the price.

After crunching the numbers it seems planning on a 10% vacancy rate and factoring in a property manager the cap rate should still be close to 20% on the buildings I'm looking at.