Again, knowing nothing about this particular company, my bet is that type of company will require money up front just to consider whether they can help you out.  

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.

If it were me, I’d run the numbers for both scenarios—how much more cash flow would paying off the condo actually give you, versus how much another investment could potentially bring in?

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.  

Yes, you bring home more each month but when you compare the amount you bring home versus how much you had to put in, the returns are typically significantly lower on your money when you pay all cash.

Multifamily real estate has traditionally been a stable asset class, and the Washington D.C. metro has traditionally been a stable market area, making the two together a good safe bet, especially for anyone with a long-term view of their investing strategy.

I'd bet on Austin over 30 years, but again, not necessarily relative to SFO. 

If you could furnish the rooms, I'd say that is best bet for cash flow.

Statistically, I would bet that many of these properties could be at risk from a similar event before the reconstruction could even be completed.What is the new premium on a $5-10-20M insurance policy and how could it ever be recuperated during the life of the policy or length of the average 30 year loan? 

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