That’s a good plan. 1031 is a bit complicated but you can continue to roll cost segregation benefits forward  

Which is a bummer since it gives me so little time from posting to sale date, but I do know banks are pretty flexible here with the sale date and are willing to push the closing date back if there is a contract in place to purchase the property.

Calling the appraiser to see what you can do to push it up a "C-Level" would be smart before doing any reno also, might only need a few things to make it far more valuable in the eyes of the bank.I've heard of a tactic for figuring out demand, which is to put up a dummy or coming soon listing on facebook marketplace and see the amount of activity you get on it. 

@Rick Albert   I may get a lot of push back from the team but I split my utilities on my ADU the conventional way....each dwelling has its own meter for water, electric and gas. 

We are looking into houses on the lower end of the scale at first to get started for a "low risk" (we could pay mortgage out of pocket no problem even if property is vacant for 30 years) house that will give us the experience we need as rental home landlords - and I am looking down the road at potential investment ideas to keep this thing rolling.

Is there any way to use the equity in my current property to put towards the new property, or am i basically stuck selling the duplex and rolling it into the larger 6 unit rental?

Not all sellers provide that but I would push for it.

starting so new, you will not be on the top of many lists as you dont have reviews that will help push you up. as you have probably seen, even with a competitive rate, Airbnb doesnt let you sort searches by price.

On a SFH home you can ask but you would be lucky to get a lease or rent rolls.

I’ve personally helped folks navigate 1031 exchanges in Phoenix, rolling their gains from one property into something bigger and more strategically placed.