So in order to continue to invest, I buy properties in a couple of cities on the outskirts such as Florence, Coolidge, and Casa Grande where the properties are below the median price point.

If possible as others have said, go to a couple of meet-ups in the area you want to invest in.

I don't personally have tens of thousands in cash on hand for larger down payments (I do though in my TSP/401k), but my dad will have maybe a couple hundred thousand after the sale of his house soon.

Recently got my Real Estate License and have closed a couple deals there in helping friends buy/sell homes, helps bring in some extra cash.

I tend to find my own properties and deal with the realtors directly but having a realtor if you are brand new to the area, is helpful. 

He was trying to move equty out of a couple of quirky rental units in Portland and funnel that into a multi-family deal down in Phoenix.

A couple other neighborhoods I like besides the two you mentioned are Washington Park, Hyde Park, Woodlawn, and South Shore.I think that area will continue to be gentrified because you have the lakefront as well as CTA trains.Is there any reason you are targeting Chicago instead ofdoubling down in Kansas City?

I acquired a 3-flat in Humboldt a couple months ago who had two units not paying (ouch).

With that being said, I probably only deny a couple of requests per year and the vast majority of guests are great!

I will be going down there in a couple of days, and interested in building/developing/investing, I am a licensed Mexican Architect, I have friends living there as realtors, US investors, and US builders ready to pull the trigger.