Also make sure the borrower is insured himself and you being put on the policy as an interested party (if I’m stating that right) in case something unforeseen happens to the borrower, you would receive a check from the insured’s insurance company 

BUT, to have a third party between you, and whomever your tenant will be is KEY.

A qualified intermediary is a third party entity or person that facilitates a Section 1031 exchange, often a trusted real estate attorney.

I really like to have a personal connection with the people I work with, as I find the process goes much smoother and both parties get the most out of the transaction.

At my properties I do not allow smoking, pets, or parties.

An attorney would decline to represent both parties in the transaction - as it would violate the right to independent counsel.  

It’s not the HOA directory, but they are “outsourcing” the docs to a third party website which stores them electronically.

I am having a hard time analyzing this as I feel it is unfair to all parties.

The entire HOA is zoned for STR so that part is covered.

Now with easier 'automating' technology you could setup a go button in IFTTT or apple automatons that when you give a certain command, it texts the appropriate party that you are out safely.