A good DST would absorb the rest of your debt nicely.

(income = 3 x monthly rent, Debt-To-Income, etc. can still be used!)

You divide that $20k by .075 and you get a boost of $260k to the valuation.Allowing you to take the property back to the bank, get a new loan with $208k of additional debt on the property, pay yourself back that investment and now you have enough cash to buy a $1M deal and use that strategy over and over while scaling exponentially.

In addition, I presented his was not the usual use case because he was unleveraged.  

And keeps you out of any trouble with debt.

Combine that with some government austerity and the debt issue improves.

The refi or additional debt of any kind will impact the current performance of your property I'm never a great fan of selling a good producing property - unless I am certain I can improve the overall performance of my portfolio. 

Like maybe I could pull enough out from heloc on primary residence to pay off debt and then rent out my primary and use the extra cash to payoff heloc and then do another heloc once the original one is paid off.

It's the concept of buying the debt attached to the mortgage rather than buying the house. 

That's before you pay any debt service.To answer your question: No, it's generally not a good idea to lose a bunch of money every month.