However, if you prioritize generating a substantial cash-flow, then Cleveland would be a preferable option. 

Look for properties with HOA restrictions that align with your rental plans, and prioritize communities with exceptional amenities.

Be prepared to make provisions for someone who may be mentally ill.My $0.02 ...

This summer has been a bit of a tough one in my area with not many houses for sale on the market, turning it into a bit of a mob mentality with people bidding over the asking price.  

Once you choose a contractor, you are walking the property to formulate a list of needed repairs/upgrades and prioritize that list - essential, high, medium, nice-to-have and cost the list.  

You need to make sure you are dealing with one set of hands to insure full accountability not piecemeal turnkey as many people have turned it into.Finally, great point, you want to maximize your time and efficiency, more than likely you do not have time to do it yourself, or even have the resources to do it yourself correctly, you want to find a good partner to work with that has a sophisticated operation and can assist you and handle the assets every step of the way, so you can enjoy your family and prioritize your time on your core job.

More importantly than the actual gift, was the boost to my mentality to keep pushing forward connecting.

Alot depends on your mental bandwidth and available time to devote to day-to-day issues.

Since a kid I was taught the Robert Kiyosaki mentality of use debt and OPM. 

If this is messing with your mental health, it's worth taking action!