Real estate is a contact sport, so the more people you get your business in front of the better.  

I don't know enough about this, and it sounds like a gamble to me.Use equity in my existing home to invest in a rental property (but this sounds like a scheme where I would take a HELOC for a down payment on an investment, to be able to take out MORE debt, meaning I have to rent or sell the investment property for even MORE money to cover increased debt costs).So, are any of these options better than the others?  

He somehow drove to my street where he jumped the curb, ran over my neighbor's "Historic Property" sign what was in the front yard...then got back on the street for a moment and then sideswiped my landlady's fancy sports car. 

New York actually has worse wind than Chicago.Anyway.. the theater scene, sports scene and restaurants are amazing.

I couldn't do the things other kids did, play the sports other kids did, go on vacation, etc. because we didn't have the money.

I just don't know how these people are making money unless they're hoping to continue to see appreciation, which is a big gamble.

I am wondering if there is a way to keep letting the kids play their sports while not needing to worry about the expenses so that I could save up.Thank you in advance.

Their scheme is now out in the public:https://www.nytimes.com/2019/03/25/sports/fox-news-clayton-morris-indianapolis.html

Is it a little more of a gamble?

We definitely sound very similar in our risk tolerance (and judging my your company name you may also have a background in "gambling").