But figure with a growing airport and travel business in Madison that could be a great idea. 

.- I had a conversation once in my owner's rep day job about new construction of a commercial building on its own parcel adjacent to another parcel owned by the same owner. 

So many more eyes trying to hinder my operation.The rural one has zero STR regulations or code enforcement but is a regional and attraction and driveable from several airports.

More regionally, Boston's STR regulations have gotten more stringent, moving from earlier proposals that would have allowed out of state rentals, to its current form allowing only home share or owner-adjacent rentals. 

I don't know why Clayton or @Scott Smith might made that recommendation - could very simple be because where Clayton Morris invest the Series-LLC is not an option.As for the attorney-CPA podcast, while a good idea if possible, I don't know if it would help you much, because there is simple too much information to cover in a 1hr podcast, with too many ramifications in all kinds of adjacent domains (formation and maintenance of LLC and business structures, transferring assets, protection strategies, trusts, anonymity, insurance, levels of risk and protection, due on sale clause, selecting an attorney, fees, checklists, etc.), and subjective to individual situations and scenarios.

While during your due diligence, work on negotiating with either of the adjacent owners for a cross access agreement.

Curious, why DC proper over another adjacent market?

There is a property adjacent to a property I own that has a inhabitable home on it.

However, the area adjacent to Briarcliff and the Northern section of 64150 is a great area to invest in and is a B to B+ area. 

Cannot be joined with adjacent.