A longer timeline will make paying the extra 2% now more attractive.

You can also contact a local alcoholics anonymous or other organizations and let them know you have space available for anyone living sober.

I live in Upstate New York but i was thinking of areas more out west or down south.

My son currently lives in the townhouse b/c he is going to school and works in the area.Since he is young and starting out in life, I would like for him to only cover the basic costs (taxes, HOA, utilities) just enough for me to break even (I believe that will put him slightly little lower than market rent rates). 

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You will be living in someone else's house.

My preferred options are:1. house-hack with a duplex under ARV; live in one unit => renovate => rent the other unit2. buy a SFH under ARV that could be converted into a duplex (preferably adjacent units vs top/bottom) - I'm assuming the biggest challenge with this strategy would be separating the infrastructure for utilities; and costly.

Even if the rental has a decent cash flow with additional flood insurance, we're still not sure we want to take on that risk as we are out-of-state investors (planning to move back to KY in the future, but not now) and we don't like that it will potentially bring down the perceived value when we try to sell it in the future.The seller has never lived there and has not provided any information on if it has flooded before or not. 

You can't rent out a PO box and live there.And yea that sounds like a huge red flag to me. 

We would be incurring the tenants in one half and would live in the other half ourselves.