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.

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.

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. 

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

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

@Mark Ainley and his team are great here.Hey @Timothy Galligan - I have several properties here in Chicago that are on section 8 and I can by far tell you the most important is having the right property manager who can vet tenants properly and knows the in's and out's of all the different programs.If you are interested in Chicago happy to make some connections for you!

Quote from @V.G Jason: The excuses people make to invest at the most casual level is appalling.I'm not going to sit here and compare lives, but trust me folks with 20x the amount of stuff on their plate can go out there and invest properly in RE by doing their diligence.