Familiarize yourself with the Fair Housing Act, which prohibits discrimination against people with disabilities, including those recovering from substance abuse.

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

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.....

There are great tenants willing to pay market rate.

Have you had any luck or need any market analysis?

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'm Kendall Hinton from Charlotte, NC, and I've been passionate about investing in real estate for 3 years; I'm particularly passionate about the high-end fix and flip market,Outside of real estate, I am a NFL vet, and currently enjoy finding new outdoor activities.Excited to learn and connect with you all!

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

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

I’ve been looking for turnkey properties to invest in (first timer) in Anywhere, USA for around $200-300k for the STR market.