I would simply hire a good civil that has done development in that jurisdiction and pay for a feasibility study and let them run through all the check items.. but thats really just the start.. also for context .. these projects require 350 to 750k in CASH up front to get to approved plat status ..

With that being said, in a worst case scenario, you can always hire a property management company to handle the day to day items if it comes to that. 

If you are on cash accounting, yes you could do that.On the other hand, you are ignoring carry-forward losses. 

But, on the other hand, if your life is very busy with your w2 job or you have a family to take care of, then maybe having a property management company will do you well and just worrying about larger items.

That said, working with an uninsured contractor still carries significant risks.

Even if such a loan existed (which I doubt), once Vincent self funds all improvement costs, finance charges, carrying costs etc., I doubt he's any better off.

There’s normally action items that can be implemented into your management process that are more effective. 

I would only recommend purchasing items that fall into that vision. 

If this is a big-ticket item, you might consider legal action against Airbnb.  

Without knowing any of your financial position of your work or side hustles it is hard to give you exact advice because you may be able to carry these homes until they are paid off and in that case they would provide solid returns, but there are likely better real estate investments out there.