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.

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.....

Have you had any luck or need any market analysis?

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.

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.  

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

There are great tenants willing to pay market rate.