So you'd be looking at high potential rental income, cheap properties or, even better a combination of the two.That prime candidates would be:Mexico and the Dominican Republic: cheap properties, mass tourism, occupancy all year long, closeness to North America, direct flights from North America, the US and increasingly Asia, strong international and domestic tourism and tourists coming from diverse locations.Southern Europe (Portugal, Spain, Italy, Greece): properties aren't necessarily that cheap (some are) but you have mass tourism there as well.Then you have secondary markets like Colombia or Brazil.

And are diversity from the IRA $.  

Biggest issue is cultural - they don't understand what is "normal" in the states! 

In the long term, I do want to diversity as well as work on the badass part (far from there now).

DFW has a diverse economy, a strong job market and good schools in the suburbs.

I think one-factor people overlook a lot is job diversity.

The diverse housing options locally, ranging from attainable existing homes to luxury new homes, allow buyers of different income levels and lifestyles to generally find what they want,” says Ali Wolf, Zonda’s chief economist.

Whereas I think the next step up for my investment strategy will be in more diverse potentially out of state areas where I can recruit third party professional management rather than doing it all myself.  

Or do you just want to shift into RE as an asset class for diversity's sake?

There are many good brokerages in Chicago, and you will have to decide who has the culture you are looking for.