But north of the river increases my commute and is not my ideal place to live.

You see, I am 60 years old and I had a brain anuerism and a stroke when I was 54 years old and it was totally not seen until just before that.  

How do I deal with it?

Maybe I've been under a rock, but I think zillow's a pretty nifty tool. When looking to buy/flip, to what extent do you trust the listings? Are there any situations where it falls short (generally)? 

You’ve learned a lot since you started the journey of investing in your first passive real estate deal: you’ve weighed all the differences between asset classes, zeroed in on your ideal geographic market, and put on your investigator’s hat to get comfortable with a few operators.

Ideally I would like to keep the majority of my investments in my home town.

I deal with used oil drums (hazardous waste) at work all the time.

Everyone has their own ideal place to live. 

Ideally you would have a property management company coaching you through your first property for a year or so.General maintenance - high maintenance tenants generally imply higher maintenance and turnover costs.

I deal with building inspectors, subcontractors, suppliers, and laborers on a daily basis.