I was running around in snow pants trying to find a store with space heaters still in stock and setting them up to heat the walls to prevent them from bursting.

The lower the price point, typically the more the competition, not less - but not always.As far as starting smaller, that is typically a good idea to prevent big mistakes which can turn into big losses as a newbie but the very low end will also be full of risk you need to mitigate as well.For the rural area idea,  would warn you that on exit, finding the buyer will be more difficult and on the front end, much more difficult to comp a non conforming property like in a rural area as you will likely not have enough comps to get an accurate estimate of the ARV.

I trust this guy, he has amazing access to contractors and vendors (from his previous career) and ideally would like to make this happen, but we would want to structure in a way that is constructive and prevents potential future issues from arising. 

What do you to to prevent yourself from getting fake landlord references from Property Management Company or Apartment complex?

I don't do any preventative maintenance unless it's a heating system that services multiple units.

You'll also want your lender to be servicing this loan themselves through the reno project to prevent delays with the draw requests.

Doesn't prevent your tenants from suing you because they slipped on an icy sidewalk.

Will giving them $30k prevent you from doing the next deal?

What is to prevent an investor from buying it and hiring someone to oversee it for $50k per year.

The city has the opportunity with this effort to implement policies to prevent both!