My main question is, knowing that there are much cheaper houses in the midwest and south eastern states that are more ideal for cash flow, what is your process for choosing an out-of-state market with 0 knowledge/experience of that market?

You may want to look into southeastern Wisconsin (e.g.

Wearlayer for residential doesn't need to be higher than 12 mil and a 6 mil will do ONLY IF you have a better scratchresistant finish on top like an Aluminum Oxide or a Ceramic Bead.

@Jesse ParkI would wrap the fascia in aluminum, and do vinyl soffits.

Look in the southeastern part of the country for what you are looking for in sub $100K homes, lower property taxes, insurance, higher cash flow, and some appreciation. 

Use the experience and connections you gain when purchasing your first multi-family to get started.I am located in southeastern VA (Williamsburg, Hampton, Norfolk/Suffolk/Portsmouth) is my region... so I'm a ways away from you. 

I have a close connection with an established home inspector with over 25 years of experience in Rhode Island and Southeastern Massachusetts.

The houses have metal roofs (galvalume) and siding (SMP), commercial (anodized aluminum windows), and top quality mechanical. 

If it’s a 1960s asset, you’ll want to make sure there is no aluminum wiring or at a minimum it’s been pigtailed at the outlets and switches for insurance purposes.

Wrap a run of ice/water shield over the edge, and install drip edge then shingles over that, or more preferably, get a single piece of aluminum flashing bent which will fit over the shingles along the top edge.