As we start to do a deep dive of the market, we would like to connect with fellow investors to get the lay of the land, insights on where to start poking around, areas to avoid, what strategies are working for them, etc.

HML outfits usually have capital partners with deep pockets. 

As many others have recommended, I would definitely do some deep research into an area to understand what housing rates and property taxes look like in the areas you are interested in.

If they could be bumped up a little then you could have a little more breathing room. 

Unless.... your happy to be VERY cash-deep into it and ready to absorb the hit's of a LOT of time delays and additional expenses or cost over-runs.

 @Stuart Udis:OK, yes new investors- not deep pockets.

If you decide to entertain this, due diligence will involve digging deep into the business financials to understand cashflow, solvency, and liquidity, his personal finances, and searching for any liens or UCCs in place. 

Do a deep dive on the property too, checking it's all clear to sell and there aren't any hidden surprises.

I chose the better policy but now I have an underwriter breathing down my neck.

They did a deep review of my listing and called me back.