I am learning a lot from BP on how to set up a property management system to begin learning the proper way to structure a rental property portfolio. 

If you buy in the proper STR areas there is practically zero regulation risk. 

or is there a more proper approach you would recommend?

Might not be easy but it has been done with proper permits here in the neighborhood.

The property is 20 mins from San Diego proper and 30 from the beach.

If  you are in the 20% range, you are better off going to the casino and putting all of your money on black and seeing what happnes.Since you are out of the area properly calculating cash on cash returns can be difficult because you have variable expenses to calculate. 

What matters is what best meets your goals and lifestyle.6.

As for the gift for the down payment, it's generally allowed, but it must be properly documented as a gift letter to the lender.

However, I want to ensure I'm properly structuring deals, receiving legal and fair compensation. 

Some things to consider with the above suggestions of creating an LLC and contributing the property + $100,000.The basis the partnership has in the property is transferred from Person A.If person A's basis in the property is $100,000 but the value is now $200,000.The depreciation would be based on the $100,000 instead of $200,000 which may 'upset' partner B.Furthermore, you have to properly structure it so the IRS does not see it as a 'disguised sale'.A disuised sale can potentially occur when Partner B contributes $100,000 into the partnership and it is immediately transferred to Partner A.best of luck