For us it's been fitness (gym/bicycling), hobbies, and travel because we're pitching pennies on rehabs. 

Perfect fit for me would be 2bed/1bath on each level.  

From there, start to figure out which markets caters best to that strategy, what your entry costs are going to be and what markets you can afford, and narrow it down that way.Once that's done, I'd then get connected with a local Realtor in that market to identify what areas/neighborhoods would best fit your needs.  

Pick a strategy that fits with your time and financial situation.

Others see the long term benefits of student housing or long term rentals that there is a strong demand for and continue to appreciate.I would just soak up some education and see what fits in your wheelhouse of understanding how they work (STR, LTR, flipping, notes, PML or whatever!)

From what I can tell the long turnaround money (rentals) is a much better fit for me than the short turnaround.

The relationship needs to be the right fit or it doesn't work.  

Seeing more deals is likely the best way to find ones that fit your wheelhouse and can make you money.

I expect the angle in Chicago with this practice, is to improve the property, but without the increased property tax implications.

Not sure the angle he's going for there.