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.

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

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).  

think of it as advance pre-marketing.  

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.....

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

More importantly, as with any market, you need to know where to buy.

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. 

Utilizing Seth's local market expertise, we quickly assessed the property's potential.