For reasons I don't yet understand, if the property is sold I cannot take advantage of a 1031 Exchange and my gains will be taxed as income, which will be 35% federal and 11.3% CA income tax. 

In the past, I cashed out my 401K(Paid income tax + Penalty).

The majority of my income comes from my rental portfolio.

More on DSCR loans: DSCR loans won't use your income to underwrite the loan. 

Here are a few strategies that might help:- Leverage Industry Benchmarks: Many investors use a percentage of gross rental income as a quick estimate for operating expenses.

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

And you'll have a solid W-2 income to help you qualify for loans. 

If you pay down $100K in loan saving you $1K in monthly costs against rental income, or you invest that $100K in something that generates $1K in net income the result is similar.

I'd be heavily focused on mitigating that future tax liabilty rather than directly supplementing that income.

Figured there would be a few data points left out of the equation' that I would need to circle back with :) .There are additional units not rented at this time which could be rented to increase the income.