The cleaning fees and platform fees combined can exceed the cost of a couple of nights at a four-star hotel, not even including the rent.That’s a problem for not only the hosts, but the platforms.

Combine that with appreciation and it could be a viable option.I also know of two different multi family properties right near the heart of Kailua Kona that are on the market as well.

Or a combination of other factors I'm not mentioning. 

However, I think if you decide to do this, you should get some money up front combined with owner financing so you have some skin in the game so to speak.

The result will be cash flow.So if you want to combine the best of both worlds, set up a small business for cash flow and invest in real estate for long term equity.

It is the only property that I own, and my reason for buying it was because I wanted to have the freedom of renting combined with an ok investment--and that's what has happened. 

My interest in investing in the construction of a new single-family residence (SFR) on the West Coast of Florida was driven by a combination of factors.

High level $200k for a $36k gross return is a low yield..however I think there are a few variables..with 35% down you should be able to get stronger lending terms, if the seller is workable you could entertain a concession towards a rate buy down for lower obligations, possibility to look at shorter duration (ARM) loans if you only intend to own 3-5 years which could also offer a lower rate.

A private lender would look to the equity in both properties combined, placing a 2nd mortgage on the existing property and a 1st mortgage on the new property. 

Once rents are optimized, the combined monthly rent will be around $4,000.