The problem with my analysis is that you will bleed tons of cash for about 2 years, but if you can hang on for two years, you'll be okay!

With that being said, Ali Boone is correct with her analysis as she suggests possibly getting into out of state investments.

I have a short term rental condo in Maui and I was recently doing the financial analysis for the property for tax purposes.

@Taylor Harrison  as far as how to analyze them I would do a multi-year analysis showing the cashflow from your time as a resident and the time when it is a full rental. 

So, your analysis says there is absolutely no reason to buy it unless there is information that you gave that is not the whole story or incorrect (did you mean 292K?)

Anyone know where I can find a Mortgage / Loan Analysis Software?

The reason you should always include ALL expenses doing your analysis is to insure the property will have good Cash Flow if you want to grow your business and need to contract everything out.  

I am now 6 days away from the end of the inspection period, below is what the complete analysis of the property looks like as is.

You then build a projection for your cash flow for however long your hold period is and then do a discounted cash flow analysis.

Here is a brief analysis comparing cost per lead of Direct Mail vs.