Some questions I’d ask and get asked often1.) like others mentioned, a major question I’d  ask is how many rentals they currently manage to see their current workload and see if they have the bandwidth to take on more properties.

Now if they got married, had kids, and a vast majority still lived in apartments that MAY have the makings of a trend.  

Have you ever overlooked a major item that needed replacing?

In some cases they may feel less bad about contacting a person vs a company.Also for self-fixes it depends on the condition of your place, but a major fix will need to be taken care of whether you self-manage or not.  

If you do have experience and connections to build then do it but majority of time buying an existing SFH works

I was raised and lived in Bloomfield majority of my life.

The city and/or fire department can shut you down if you violate zoning.

We are in a semi major metro (Tampa) so while labor is always challenging it is not as difficult as a small town I imagine. 

Detroit is the poster child for major city declines.

I know Kilington and Stowe are strong but I thought being a little closer to major metros might help and the info I'm finding seems to support.