Taking on deals like this that decrease wealth, such as low return high upfront cost whole life insurance, paying 19% interest on credit card debt, paying 2% annually to have a “wealth advisor” place your money in Vanguard Index Funds, paying for a high cost mortgage because you’re credit is bad, and “debt consolidation” programs are all reasons adding up to why many people can’t achieve financial independence and remain dependent on working every day to live paycheck to paycheck.There is a chance that in a particular circumstance any of these, including the program offer you describe, can be beneficial in certain specific cases.  

On Hawaiian island, the number of visitors to Hawaii from the mainland US decreased by 10% but specific islands like Maui got hit the worst by 30-40% (?).

Had a nice positive cashflow until approximately 1 year ago when I had increase in property tax and HOA, plus had  insurance increase, which decreased my cash flow to nearly $0.

I would qualify it with in today’s seemingly rate decreasing environment, I might look to trying to recoup costs in 12-18 months (or less) 

Those two things will result in higher payments and decrease cash flow.

Now, property values have dropped—almost to the point where the capital gain tax I avoided through the exchange is offset by the decreased value.Has anyone found an effective 1031 exchange strategy that allows you to take advantage of the tax benefits while still buying the replacement property at a good price?"

If you're switching from STR, you should expect a decrease in ROI since MTRs earn less than STRs in general.

(I have five rentals).Thanks What Russell said, you can decrease that liability as much as possible on making sure you line out the 593 form. 

A few weeks ago we decreased the list prince by 5%. 

Avoid anything with condo association fees or homeowner association fees as they DECREASE CASH FLOW with no real contribution to the bottom line.Lastly, since you are new, when you do get a property DO NOT HIRE A PROPERTY MANAGER.