I highly recommend you checking out Guesty in the meantime as it sounds like your main issue is scheduling cleaners, when really, there's an easy solution for that.Book Rec: "ClockWork - Design Your Business to Run Itself" - by Mike MichalowiczSide note - Matt I'm jealous of you being in Kihei, I was there a few months this past Spring, beautiful place.

The property, located in a desirable rental pocket, boasted three bedrooms, one and a half bathrooms, and functional central heating and air conditioning systems.Our financing arrangement spanned 30 years, resulting in a monthly payment of $990.58 covering principal, interes What made you interested in investing in this type of deal?

An Air BNB COULD be active and subject to SE- however it really needs to be fully operating like a hotel, offering much more in terms of services than what most offer.

Hard Money Lending/Private Money through Spring Garden Lending How did you add value to the deal?

I'm in Spring/The Woodlands.

I will also be selling a second property this spring, also a single unit (SFR), since I stripped a good amount of equity from it a couple years ago through a cash out refinance to purchase a triplex. 

(I'm personally happy this failed because I have two clients under contract on homes they plan to short-term rent -- one in the mountains outside of Colorado Springs and the other right near Breckenridge.) 

Yes this was a air bnb booking. 

Any thoughts out there about a couple of things: vac rental market in these areas, taxation, overall insight, etc. we have secondary thoughts about Big Bear and Frazier Park, CA, but investment market is very tight here with Palm Springs area mostly closed out.

We are right down the road (I4) from you in Tampa - are busiest month is spring training spring baseball so late Feb into March.