I've got 2 condos, a 2 bed at Maui Banyan and a 1 bed next door at Kihei Akahi.I'd definitely agree with @Patrick Franta - from my experience as well, the 1 bed unit has performed better.Also props to @Mike Neubauer for sharing his knowledge and experience with me - I'd definitely recommend you take him up on his offer if you have questions etc.I recently heard that the County of Maui is considering a ~50% increase in property tax for short term rentals from the current $9.37 rate to $15.41, equal to what time share units pay.

I remember chatting with a good friend of mine, Jared, who once picked up a quirky three-story in Somerville to rent short-term.

We bought it as a short sale.

You can do a trial and see if bank feeds connect, if it does, I would then recommend using it over QBO.One of my client that just started in development is short on funds so Xero was the only best option and they are using a local bank so we couldn't connect and a lot of manual entries. 

I would have to do a small rehab of floors and paint and maybe new appliances.I want to do short term rental or this if possible.

@Rick Soto,Both options have their pros, but here’s a way to think about it given your plan to move in 5 years:Option 1 (10% DP, 2-1 Buydown): This gives you lower payments for the first two years and saves you cash flow short-term.

Long story short, I am in a bad financial condition as of recently.

You need to drive short distance on private street and then up ~150’ driveway.  

Such units are painfully in short supply and sky high demand.

The short answer is YES, they would have you cancel any and all rez that's for 13 or more.