It could impact your home equity and financial security.For a safer and more specialized alternative, consider a Fix & Flip loan. 

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.  

Unless you are unknowledgable, my bet is you could make more from rent than sale, and still have the benefits of owning the original home while you go do something else.The 25K you have left in property will be netting you(gross) of $350 mo or 4200 per year.

But, I bet-ya it's also effective.  

I bet we would have made around $100k as a wholesale.

I doubt you'll make 11% with the S&P, but it is probably still your best bet.

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

Airbnb gives you the best bet at getting both. 

Best bet is to carefully analyze the zoning maps and regulations or just call the town and ask.

Bet they're making their car payments (walking sucks!