Will my slight decrease of cash flow be worth it?

If you're barely paying P&I, I would suggest raising the rent, and decreasing landlord costs.

There's only one way to improve DTI on a loan application - add more income or decrease the outgoing debt.

Even if they balk, it exercises your creative muscles. 

Pay off one of the mortgages which would then increase their cashflow and decrease their expenses meaning they need less reserves. 

@April TsotsosI think as we age, our risk appetite decreases, especially since our W2 income stream is coming to an end. 

Your money is whatever balance you have in your account, if you bought stocks or options and they increased in value, their current value is yours (same if they decreased in value).

And the gross rental income that you would decrease by 75% is held against the debt loan for that property, meaning taxes, insurance, HOA (if applicable) and the mortgage payment. 

So the plan would be to refinance my primary residence to get a lower rate and decrease my Debt/Income ratio ( and just to take advantage of these low rates)    Then either 1) get a cash out Refi on my other property for ~ $65k to fund the down payment for a new home and get a decent rate on a loan OR 2) GEt a HELOC to use for the new property's down payment (and finance at whatever rate??)

It's true condos in that area do can take longer to sell, without much of a decrease in price.