Once you understand a little more about the legislation and laws in place the tenant laws will not be so scary.For a 10k a month cap rate you are looking at inventory that would either be a luxury single family home or a multifam that would be 4 or more units.

DSCR which has awful rates unless 25-30 down is an option.

Some will argue that prices will only go up as rates come down.  

I keep hearing this is predicted to be the most active hurricane season of all time.As if insurance rates weren't already bad enough in Florida and coastal areas.

We are hoping to retire to this home in 2-10 years and figured we'd buy why rates are cheap and let someone else pay the mortgage for awhile.

It's not unusual to have tenants paying $800 pm what would be a $2000 plus market rate unit.TOPA in any of the jurisdictions that have it doesn't really concern me.

Interest rates are a bit higher than conventional loans, but definitely worth looking into.  

Super Jumbo mortgage loans and lenders can vary widely in their rates and qualifications. 

I am looking for one that:- provides checkbooks, and - pays a decent interest rate.

Based on both of your posts I’ve done a little math and calculated I would have to charge $255 a night (at a 44% occupancy rate) to stand the smallest chance of making what would make this worth it to me.