I've had them close in half that time, and I've had them drag on much longer.

NVM it is about an hour and a half away from Tampa, FL

I would love to have a project lined up right after the settlement day for the second property that won't require 20% upfront costs, if possible.If you can buy a property cash, or through a LOC then that will be easiest and most fast.

Based on the area, I have about half the amount I need to buy the land and build in cash but of course I’d love to finance the entire thing with as little out of pocket money as possible.

The insurance is half the price and the home should have much better bones.

The commercial loan on the 6 unit would be the easiest to complete and the lender would rely on the NOI of the property and not the market compsAnother thing that I think of is maintenance.

With my father as well of course who I believe would definitely want in as he also owns half of our "spendable equity" that we have available.

You can find great looking tile for half that price at home depot and it will last 3x as long.

I also assumed you'd be living in half as that is the only way you can do it with such a small down payment. 

@Bradley Padula I've tried this, however, the most recent duplex sold in the area is around a year and a half ago.