Usually its a safer bet.

That’s the best bet.

I do not see that home prices have dropped 2-3% and this is a lot of added savings in additional to a downpayment if so. 

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.

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.

I should add it will be a short term rental property. 

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.

A PM offers so many additional services in addition to things you cannot do yourself - like simply having a 3rd party between you and the tenant.

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