Run the numbers.

Second part of the question - The "VERY BRIEF" conversation I had with my mortgage guy a week ago was "a cash out refi will be better in the long run". 

We run a Vacation Rental Hosting & Cleaning business so we have a lot of experience with Waikiki condos.

However, you still run the risk of getting so busy with your regular job that you lose sight of the rental and things slip through the cracks or you don't have time to deal with late rent or you forget to do an inspection...A property manger costs about 10% which is $2,400 yearly on a $2,000 rental.

This is because traditional banks/lenders are going to go off the income you report to the IRS, which especially for small business is typically really low after expenses/write-offs (investors often run into these issues as well after investment property write-offs).

They fund, I run the business, I make my cut. 

Could you run BRRRR in the zone, the property must be purchased for cash.

I run a commercial recording studio and she owns a hair salon.

This protects you in case the tenant leaves a garden hose on and runs the bill up to $300.

Run the numbers.