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

Mainly homes in good school district.  

@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). 

Suggest you go the electric route--less or  no maintenance costs, and when repair is needed, inexpensive compared to most gas fired boilers or furnaces.I would also have a small natural gas wall space heater installed somewhere on the main living floor (not in bedrooms) just in case of power outage and / or for supplemental heating.  

.- He then sells me a portion of the LLC for $500K.I see some pros and cons to both scenarios, but I mainly want to make sure that I follow the established process.  

Wholesaling Lease Options will be our main niche in our REI business.

Are there other factors we need to consider?

With the rental property, my main goal is to find a Duplex and house hack it, so I can learn how to be a landlord and get some experience under my belt. 

Mainly, I've been looking at the MLS and Zillow (FSBO) without much luck. 

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.