Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

Therefore, your financial freedom hinges on new companies continuously moving into the city, creating replacement jobs.Companies have many options when selecting a location to set up operations.

Airbnb gives you the best bet at getting both. 

Well the bet I'm making here is that CapEx and repairs will be very low the first few years (honestly event he first decade), and once all the construction ends I will be able to increase my rent closer to market rent at $2k which will give me a better cushion.

Best bet would be a “partnership” with a monied individual looking for a high risk/high return passive investment with you providing the “active” part.  

I bet if converted BACK, it would be 4br+, probably a rather spacious 4br+: - a whole lot easier to rent given much more demand for such vs efficiency or 1brs- no longer competing in any way against apartments- no more utility issues, because tenants cover 100% of there own utilaties- no more headaches of wrangling different persons to play nice togetherAnd on and on and on...... 

DSCR Cashout is your best bet!

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

I'm betting he'd drive to that area.

You might have to dig into off-market deals, though, since inventory is tight.Multi-Family: Always a safe bet if you can snag a good deal.