I am a real estate agent in the Columbia,SC market, but I actually starting investing 2 years prior first.

My main questions would be: how long does the entire process take from applying to actually having possible tenants to start picking from, and how do they determine exact amount for rent (the amounts listed on the housing authority site seem way higher than market rent, I’m wondering if I will actually get those numbers or not)any other general tips or advice is also appreciated!

@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?

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.....

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.

Have you had any luck or need any market analysis?

There are great tenants willing to pay market rate.

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. 

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