And Island Experiences like Trap to Table, hand-cranked Ice Cream Socials, Expert Talks, Baking with the Innkeeper, Sunrise Breakfast Hikes, Cribbage tournaments, and more.  

STRs that are not the absolute peak performers are already having issues with vacancy, and AirBnB recently changed their platform so that only the absolute cream of the crop units (five star resort-level luxury units with thousands of perfect guest ratings) are getting promoted.In a nutshell, STRs are a lot more work, require a lot more expertise, and are a lot less reliable/secure than traditional long term rentals (all other things being equal).Plus, house hacking a long term rental will give you invaluable experience in how to analyze, acquire, and a manage a property that you can then apply to doing a STR in the future (if you decide you want to go that route).Start with the strategy that is the easiest, simplest, and most likely to succeed (house hacking), and then gradually build up to more advanced strategies (like STRs, BRRR's, etc.) as you gain experience.Good luck out there!

80% of wholesalers go out of business leaving the top 20% cream of the crop?

However 20 years from now I’ll still be glad I didn’t jump out of a airplane without a parachute, go swimming in a pool of piranhas, or eat liver flavored ice cream

When you go and sell it later down the road (not as a primary), you are going to get absolutely creamed on taxes. yes, you can still 1031 and defer taxes, but it's just a deferral.

End of the day its tourist based.. if I was doing food cart I would go for the Snow cones  the guy who has one the one in Kihei kills it.. so do some of the Ice cream vendors. 

I am hoping you can share how to sell so many homes in the same calendar year without getting creamed at tax time? 

It has a new roof, new heating, new air, water softner, security cameras, networking, and ip phone system, on top of granite counter tops, and a ice cream bar with about 5 to 10k worth of custom cabinets wood shelves for medicine display.

The cream does rise to the top.

I'd paint everything white or cream.