Also, it's hard to time the market... e.g. if you sell your house at the 2 year mark, you are going to rent & wait for the market to show a good deal, which is a gamble.

Given that rates are very low currently, is it worth it to gamble and hope that rates are still low when we reach 20% equity?

Its all a gamble , its investing , sometimes you win sometimes you dont .

@Matt M.So these people that are doing no inspections.... they are just gambling that there is nothing wrong with the property?

A handful allow a month or more...not day by day....some people say renting 30 days or more to one tenant can change the STR to someone with tenant rights, so some operators won't do that.I've also seen condo associations prohibit or restrict even LTR, so that does happen.You could be entirely right that state law supersedes HOA CCR and R&R, but is that a fight you want to fight and pay to fight and gamble on big lawyer fees?

It's all a gamble, barrier of entry aside. 

In Hawaii, you're mostly having to gamble on appreciation, which is just that -- A GAMBLE. 

Any pointers before entering the Maui real estate market as an offshore investor?

No idea what my roi would be, it would be a complete gamble.

Whenever I receive a booking, my offshore assistants double check all calendars to ensure no double bookings.