Quote from @Nate Marshall: Quote from @Robert Short: This is my concern as well.

For more expensive properties you'll be wanting to pay a lower interest rate and doing short/mid term rentals.

My suggestions would be in this order:(a) Determine the type of financing you qualify for - this will short cut the process considerably and save time on investment angles and next steps.

Even if the property is short, a contract with a buyer, even subject to short sale approval, should work. 

--------------------------------------Context:-My wife and I file taxes jointly and own 4 long term rentals in NJ and 3 rentals in FL (1 long term, 2 short/medium term).

More insurance will cancel short term rentals.

With the upswing in the country's short-term and mid-term rental markets, a unique opportunity is presenting itself to house hackers during a time when it's harder to cash flow than it was a few years ago.

I don’t want to die in any corporate job.3.I want a long term goal, a midterm and a short term.

I wanted to get feedback on managing short term rentals in Hawaii. 

They are bought either with SHORT term high interest (hard money) type loans or purchased in cash.