Again, I do not want buying the multi-family home to block me from accessing lending for the second home when I move.- Does anyone see any flaws or can offer some improvements/considerations to the financing strategy of this plan? 

With land investing/flipping becoming more democratized/accessible  (so many landed courses, tools, resources etc), current prices/RE trends etc, is it still worth getting into land investing/flipping for a brand new RE investor ?

I have access to AirDNA and it has its shortcomings.

On one project we did we proposed 36 highway accesses and were denied as been excessive. 

Even when you buy a property with tentants, you also have the risk that they stop paying you and since you didn't screen them, you are left with just hoping they won't do that.

I'd like to bring him in to assist with the renovation expertise as well as access he has offered to his labor pool.

You’ll see the appraisal that you may have access to and what it sold for was more than inline.

Small shop brokers that have access to multiple programs so that they aren't beholden to one or just a few loan programs will typically get the most competitive product for the borrower. 

The property is in a great location,  close to stores, restaurants, fair grounds, freeway access, and less than a mile from hospital.

Google NMLS consumer access website.