Because of the relationship between lower housing prices back in those years, and how rents have increased since, we have good cash flow on our portfolio.  

Ugh.In all seriousness, I think for $50,000 with a 1200 square foot house in Michigan should be able to modest rehab.

I would like to sell a couple properties in the future, would I be able to use the 1031 strategy to buy one house that I would use as a primary residence?

What rentals are not subject to fair housing law?

If you don't/won't have WiFi then you should either consider a SimpliSafe system that you can move around from house to house, or some type of Trail cameras like hunters use for identifying game areas.

I currently have a 4/2 SFH/LTR/Section 8 house under contract and I am getting quotes for property insurance.

Free healthcare free cell phones free housing.  

We all assume this isn’t a house you’d buy with your own money.

(Previous rent was $1,300 but we're about to put in a brand new kitchen from the studs, new flooring throughout the house, new furance, adding A/C, etc).So do we just pay for it all upfront and mostly drain all of our savings, or do I let the rent pay for it and utilize our other savings to get a second property this spring/summer to increase our cashflow? 

This is an obvious fair housing law violation because you are choosing which prospect get the concession.