Current ownership was not local, and didn't have a presence anymore.

If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.

That said, be sure to check your local jurisdiction for other regulations.

Much of my career for the last decade has been in Cybersecurity, and we feel the same about DOJ and regulations around incidents. 

@Eric Andersen definitely put weight into what @Michael Baum wrote and do your own research on the city regulation/zoning.

That could mean fewer lending regulations overall, which would be amazing.

As a newbie, I’d love to connect with local investors and agents to learn more about the area and refine my plan.

Rare do I hear of recommendations but I do hear people asking.I would think in any big city you think about, a visit to a local NARPEM meeting or 2-3 visits would be a great idea. 

Understand Chicago ZoningChicago’s zoning regulations vary by ward.

There isn't a sustainability problem in Texas, it's a regulation problem.