I don't see the value in this unless they actually provide a way for you to obtain off market properties.  

I'd ALWAYS go through an Insurance Broker to obtain a new policy!

A muchlarger floor area is possible by obtaining a density bonus forincluding a few affordable rental units. 

Current car: Kia Sportage 2011; let my girlfriend pick it...Dream car: 2012 Nissan GTR, it seems obtainable for me one day, unlike a super car...

My goal is to obtain a property requiring rehab while living in the same property for the first 12-18 months. 

Aim for expansion by establishing clear objectives for growing your holdings, like obtaining more house hack properties or branching out into other real estate categories.

They aren't tax savvy and neither are high income earners (both very low income/retired) and won't really entertain any savings strategies.

They would need cash to buy/rent seasonally in Florida, so is there a scenario where they sell the house to me, obtaining the cash they need to buy in Florida, and then rent one of the units back from me in the summers?

You can also obtain a DSCR second mortgage if you have trouble qualifying for a HELOC. 

If I were able to obtain another loan for $200K, even at the same interest, I can pay that down and off over a few years, and then I'm back to my low interest loan only and a ton of equity in the home I could potentially tap into as well.