As an agent I would not want to touch this with a ten foot pole due to the risks.

Getting your foot in the door here is the hardest part, so you're lucky to have family willing to help.

A good example would be that current zoning laws require a min lot size of 20k sq foot to build a duplex.

I am looking for guidance or someone to partner with, so that I can get my foot in the door. 

Just by owning a drone I feel I already have a foot in the door.

I have yet to step foot in the home so there are many assumptions and unknowns at this point.

I find it ironic that those who claim to "care" about others are usually those who are already taking more than they are receiving and what they really think is that everyone else has to foot the bill them.

I agree with @John Warren definitely don't use a "by-square-foot" number, and definitely do your best to actually learn rehab costs locally.Here's an actionable suggestion: Next time you contract a house, invite all your buyers to see if they're interested in purchasing.

I'm finding that the NYC & Southern CT markets are very saturated making it incredibly difficult to get your foot in the door.

This is a tight line to walk because you don't want to shoot yourself in the foot.