It's great for cashflow and our entry level costs are lower than a lot of other markets.

There are both guidelines and laws at local, state, and federal levels.

Screen them to determine a level of risk, and then decide if and how you will mitigate the risk.In this case, the risk appears to be an eviction from five years ago.

Quote from @Polat Caglayan: 1500 sq ft and a mid-level renovation that complies with section 8 standards I would get a contractor out there 

I do understand being selective on the type of buisness you take, but as an agent we still have a fiduciary duty to our clients to make sure they receive the level of service this price requires. 

Who else has had to push through setbacks to get to the next level?

I'm kind of a purist, but I'm hesitant to put in an all new floor (pull up the old ones, level the new wood flooring on the beams) because A) It's expensive B) it's a loud, big job and I have tenants on the floor below. 

Additionally, any existing restrictions at the town level (there are MANY) will be abolished, unless deemed "reasonable" by the state.

For financing, there are programs like FHA loans for first-time buyers, and there may be local or state-level programs offering incentives for affordable housing investments.

Furthermore, how important will be to have one of our team members providing oversight of the development process and what level of oversight is needed if the first option is selected.