These cities literally helped build up this country and our economy and I will never understand how much negativity they receive for fighting through adversity and playing the cards they're dealt!

As for the single family with ADU, it is not a duplex but most of the adverse LL laws do not refer to the 2 units as a duplex but MF or 2 units.  

I’m not entirely sure I’ll ever be able to get her on a mortgage because she’s just so adverse to having debt.

I currently broker LIHTC multi-family for a large firm coast to coast and am also interested in MF in the Arizona submarkets as well, and will eventually invest on that scale - I just figure breaking into the state through SFH flips may be a more risk adverse way to understand the pros and cons to phoenix submarkets.

When ready, start with a small property, near home, with enough capital in reserve to handle adversity.  

A lot of things to think about that good agents should be doing for you just in regards to checking open or suspended permits, liens/rolling fines, is the property condemned, any outstanding issues that could be adverse to you.

I am a risk adverse investor who prefers conventional financing on properties which requires 20% down for single family properties and 25% down for multifamily properties. 

I would upgrade properties every 12-15 months as allowed by low down payment loans if my significant other wasn’t risk adverse and opposed to moving.

Oklahoma adverse possession law   If the neighbor has notoriously occupied it for a period years, in your state 15 years, he has legal claim to it.

., and I still love Cook County because I have a solid team and underwrite deals properly.I think @Paul De Luca nailed it on the head, though - it seems like you are quite risk-adverse, so maybe given your risk tolerance, it's not the best idea, but if it were me, I would not think twice about it, and find a rock start property manager who knows exactly how to vet tenants.