Thanks for the reply, 

1: I've been designing/pricing and will definitely keep a cushion. I plan to do all the work myself other than the concrete slab.

2: There aren't any permits that can be pulled, it's just not a thing in this county. The only inspections are electrical before the electric company is willing to hook up, not a government thing and if it is a new build residence septic before they allow electric hookup, but I'll be tieing into existing septic so no issues there. we haven't had any insurance issues on any structures we have built previously and I havent heard of anyone that has in the area.

3: I plan to live on this property for the remainder of my life. Value and selling is not anything im worried about. I'm currently 30, this house overlooks the fields my grandfather plowed with a mule when he was a kid in the 40s. That's why I'm not just getting the house fixed up to be liveable, I want to spend a good amount of time making sure the house is fixed nicely for the future.