If she wants paid for canceled appointments, then I would suggest you look for a new cleaner.My policy is to keep all funds if the guests cancels within two weeks of their stay, unless I'm able to rent to someone else for the same period/rate.

Lenders typically look for a DSCR of at least 1.25, meaning your monthly rent should cover the loan payment plus 25% more.Seasoning: Some lenders may require a waiting period of 6 months or more before refinancing, so check with your lender to see if this is an issue.If the numbers align, refinancing could allow you to recoup your $136k investment without selling.

I am curious though, in hindsight, how does an investment in STR in Hawaii in 2012 would compare with other markets over this period of time despite all the regulation headwinds?

Period!

I've had some investments perform better than others but section 8 rentals were the one that were most challenging to sustainably operate and my worst performers over an extended period of time.

There are some buyers that are just a complete terror during warranty periods with expectations that are not at all aligned with the purpose of a builder warranty.

I think this removes the mortgage from your DTI, but there may be a waiting period.

For what it's worth, I went through 5 different property managers in 2 different markets (one local, one out of state) over a period of 5 years, before deciding I would self-manage everything across both geographies beginning last year.

I have never seen a judge turn down a request for more time for a qualified sale, unless the homeowner has already abused the system for excessive periods of time.

So I'm not sure how long of a loan tenor you're looking to offer with your owner financing sale, but my advice would be to use a higher interest rate while trying to keep the monthly (or whatever other period you use for payments) low.