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.

Hope this exercise illustrates the fact the BRRRR and cash flow are not always indicators of success and far less time could have been invested to achieve a more favorable result by purchasing in Market A at the start.

For instance, given the proof of work concept used to verify transactions, there was an inherent limit built into Bitcoin that would preclude it from ever becoming a high transaction currency.  

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. 

In the years that I've represented primarily BUYERS, I find that there has been challenges navigating transactions where the seller is a For-Sale-By-Owner (FSBO) AND inexperienced in handling a real estate transaction.

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.

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?