I was in Indy this past 4th of July and saw the exterior of properties and drove the different areas.Shawn I did research the well/septic issue and that kind of reduced my concerns about potential cost to convert if required.  

First, you can syndicate the equity portion, which reduces your own required use of funds.  

I spent 3 years reducing my expenses by over 50%, paying off all of my debts and growing a small nest egg.

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.