The process is determined by your state landlord tenant regulations and is specific to each state.

Someone looking for a duplex may be inclined to rent an apartment as well depending on how strict qualifications are.I hate to use the Alphabetical rating system because it is completely arbitrary and often abused for the benefit of the seller and to the detriment of the buyer. 

Is anyone familiar with ( OR Where to find) the Short Term Rental regulations for Southern Pines, NC.

So you need to look for properties not in HOAs or in HOAs that allow/regulate short term rentals or dont mention anything about them in their CC&Rs.

I do not have any experience with historic homes, but I have heard that you need to be aware of any restrictions/regulations if it is in a historic district.

The reason is that RE is difficult to administer due to regulations and tax laws.

Wow....why would I want to spend all of my time and effort doing strictly sales when this person who is buying this property will be generating approximately 100k a year in passive income from it?

Honestly if they need to store a couple suitcases I wouldn't mind, but it's easier to start strict and go more lenient afterward then the other way around.The second is most tenants are not careful about things in the attic like A/C duct-work and will lay or drop stuff on them causing damage and possibly extra wear on the unit since it is now cooling the attic instead of the living space or has restricted flow.

"Trust" is a word that implies a legal function or arrangement that is highly regulated.

So yes, “cost of money issues are mostly fungible across same type RE investments”, but looking strictly at the cost is very narrow sighted to the OP.