In my opinion, you should identify the new asset you want to acquire first or make sure there's an adequate supply before selling your current asset.3.

Go over it slowly, highlight the really important parts  and be very clear with expectations and possible consequences.Second-  Do  a walk through video  (3-5 mins) clearly showing the condition of the house at the date you acquired it, open blinds, show smoke detectors, show any damages-- anything good or bad.   

@Ryan Runchey If you are planning to scale up in the future, then QBO is a good option and you can start with the lower tier subscription for a single property, you can upgrade later when you acquire more properties.

Go through the process of acquiring a property by submitting an offer, bargaining the terms, and collaborating with experts such as real estate agents, inspectors, and attorneys.

So I am in the process of acquiring a new property in a good area that is vacation driven in upstate NY.

We are now interested in acquiring a STR in the Disney Corridor of Southwest Orlando .

I've been acquiring and selling real estate for well over 20 years but I've never acquired or built a duplex. 

The concept seems better than new construction in terms of project time, but I'm wondering about the cons to this idea with exception of price being an obvious one.In theory it seems scalable and efficient, in my mind acquiring the land suitable would be the hardest task.

I beleive this is an important distinction because you appear focused solely on apartment buildings that were acquired because of favorable debt or other bad projections. 

I'm planning on acquiring a HELOC on my primary residence to help me with the down payment/expenses of my first investment property.