I want to minimize my taxable income for the year.

I also don't think the price would be cheaper then preexisting homes.

Hiring a lawyer sounds expensive, but it is way cheaper than hiring a amateur (in this case yourself) who costs you money and provides no results (and then you need to hire a professional anyway).My personal philosophy is to "do it right, or do it twice" and its way cheaper to do it right once. 

I have to choose between a much cheaper market that I live in that is much easier to cash flow, but finding good renters could be more difficult.

Those are probably cheaper than hard money anyway. 

Duplex can always add additional units via the ADU laws. 8) Related to number 1, purchasing a property with an existing ADU is cheaper than buying a property and adding an ADU.

In your example, $250 in utility bills is much cheaper than $2500 to fix frozen-pipe damages!

Are you trying to hand your “friend” a 50% taxable gain that you’re going to keep?

Duplex can always add additional units via the ADU laws. 8) Related to number 1, purchasing a property with an existing ADU is cheaper than buying a property and adding an ADU.

Labor is much cheaper than other parts of the US.