@Pavel Ushakov and @Oscar BrooksAny indication how much your taxes will drop because of the decreases?

The real estate crash of 2008 really started in 2006 with increasing inventory that lead to decreasing prices.

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. 

Next time, if our in-house staff is too busy, we will sub out more to decrease holding times.

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??)

Personally I would keep in discussion with the seller, but wouldn't pull the trigger unless you have some favorable terms in there, decreased price, etc. 

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

Putting it on the market and hoping the market hasn't decreased, which it sometimes does.On the other hand, I've really enjoyed buying places and keeping them long term. 

I agree with @Chris Mason it will be nearly impossible without proof of consistent income over the past two years even though your rental income will decrease your DTI banks want to see the income. 

You can either decrease expenses or increase rents to have a higher NOI and thus a higher property value.