@Peter TrifanI would reach out to as many brokers and property management companies in your market for recommendations.

Not sure if I should stay in the Chicago market or Invest out of state in a more land lord friendly state?

I have a limited view to the 3-4 markets in which I invest, but I don't see any long term rentals in desirable locations that cash flow year 1.

It's sell, take the 100k profit, your at 360k in the bank, VTSAX or money market and chill for a bit, see how this market/economy thing plays out, rates have to come down no one can afford at these rates, then maybe look to refi and get the rate under 5%.Also something to think about.....

Have you had any luck or need any market analysis?

You need their analysis, understanding of marketing, and access to the investors (especially if they also do property mgt).  

My wife and I have been investing in the stock market for retirement for years and we are hoping to diversify our investments by getting started in real estate. 

I started my real estate investing journey this year with the private purchase of a off market house that went awesome.I then found a interesting triplex/warehouse property, went and looked at it with the listing realtor, crunched the numbers and decided that it made financial sense.

think of it as advance pre-marketing.  

However, if there are utlities in that market on 30 or 90 day billing cycles, that could be the issue.