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.

Typically, you can only do one rollover per 12-month period (again, IRS Publication 969 has the details).In the end, having the option to invest your HSA funds is usually a better bet than letting them sit in a basic savings account.

You're best bet is to call a few brokers local to the area and see what they can come up with.It's definitely going to be a surplus or excess carrier that will do it and the premiums will be high. 

I’m not a betting man.

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

An experienced broker with lots of choices at the palm of their hand is probably the best bet.

Clearly, shes not happy and an unhappy tenant usually results in more issues down the road, and you can bet they'll be expensive issues. 

It's a stalemate due to affordability and either wages or prices give, I would bet the latter. 

You could certainly reach this demographic, but it could also cost you substantially more than the return.For the money, your best bet is probably a dedicated website for your property with the key words that you want to convey.

Nothing is a sure bet.