This can reduce the impact from my item #1 which is the primary reason ADUs are such a poor RE investments. 

I served ten years in the Army, during which I spent 3 years deployed and was medically discharged in 2010.

If they were all roommates and one had (non-medical ) judgements against them I would refuse.

In my opinion, you're doing the same thing with your 13 cities. 2-3 days is better than 24 hours, but not by much.Would recommend reducing it to a city/week and setting up appointments to see several properties in each city, to get a better feel for where you want to invest and who you want on your team. 

I never worn the landlord hat and have no experience with what this transition would be like.I am definitely okay with taking a hit on earnings to reduce stress for myself and minimize problems.

I'm looking to house hack -- live somewhere, reduce housing costs in year one, then turn that property into an investment property in year two or three. 

As I planned to come into huge equity gain from the sale of my house I already know the basic of getting back to zero with taking out all the debt and I have been able to reduce my spending immensely.

My wife and I spent the last 5 years paying off $150k of debt (car, credit cards, student loans, medical bills, etc.).

I will write the property under my name and, hopefully, later would refinance it to pull out some cash.We're in a good relationship, so there are no worries regarding stealing money from each other or anything along these lines.My main concerns are tax-related; is that a taxable event, how much, is there a way to avoid/reduce it?

Bigger projects like problematic older malls in good locations are being transformed into medical type buildings close to universities.