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.

@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. 

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

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?

Now I own a successful rental portfolio.

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 do that and success will be inevitable. 

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

If you're not careful, the administrative requirements can trip you up—but when done right, the savings can be well worth the effort.For those of us scaling our portfolios or actively managing real estate deals, the conversation about structure isn’t just theoretical—it directly impacts how we protect our wealth and position ourselves for long-term growth.What I’ve found is that many investors don’t realize how critical their personal credit is in setting up these entities successfully and accessing the funding they need to operate and grow.

It's good to hear others are having success, but I would check if it works in your area before you spend the $150.I don't know if this would apply to you, but some folks think that FF works similarly to AirBnB or Vrbo where they will push resident requests to you.