I have no idea what this guy/company does, but he may be conducting activities that fall under SEC's jurisdiction. 

In future, there might be some complication if you conduct both activities under same LLC. 

The lease could say that you can only conduct the business you tell them about (e.g. lawyer, accountant, consultant, sales, etc.). 

This is a business solely operated and conducted by myself.

If you are really serious about the investment, use title company to conduct title search on the property to get a whole picture of all the liens and chain of title history of the property. 

I don't even know how one would typically conduct a search for a place.

I've seen other posts that suggest conducting an ARV analysis to get this answer, but I just don't have enough experience (or confidence) to trust the results that I would achieve.

I will not buy anything until I conduct a personal visit there to survey the cities/neighborhoods and interview realtors & PMs. 

We are conducting market research to see how the vacation market responds to this product.The first 5 vacation rental owners to inbox me will receive a Bath Caddy.

I will hire someone to conduct a CMA and see where things are by then.