Although management has always been the key to success or failure. 

There are a lot of variables to consider so it's impossible to say if investing in one of those other markets would have been "better".However, I think you could make a stronger case that you have been (or would be) more successful with your real estate investing in Chicago compared to other markets.

I would like to buy my first rental property in a few months and am doing some research in order to be as successful as possible.

Let us know what you end up using....and what success you have.

My question is what is the market like down there for successful rentals?

@Scott Shumardi can't answer your question, but here is my recommendation.  1. start going to meetups and find out which HMLs the successful investors work with. 

I’m Daniel Vargas, and I'm well experienced in Real Estate wholesaling, While I can’t promote my company directly, I’m looking to connect with cash buyers in the South Florida markets such as Palm Beach, Miami, and Broward, I’d love to hear from anyone who has successfully built relationships with investors there.• What strategies or platforms have you found most effective for connecting with them?

This is what you are trying to do, but you want a chart to tell you which means you don't have the time to put into it right now to be successful.

You will also be able to show you have good cash reserves, good credit, a W2 (they don't care about job gaps) and you were part of a successful Joint Venture with an experienced fix-and-flip investor.  3.

Now I own a successful rental portfolio.