I have been doing this for 20 years and make a modest living. I do not make 50k a year but I never had a goal to do so. I'm not a go getter and don't want to be.
So my experience is not typical nor helpful to you but what I know may be.
I do know a number of go getters like yourself. And I know the owner of a long term a successful mower shop who knows and has talked to many many people in the business. So I hear a lot of whats going on.
Most do not make it. For every guy on here your talking to that did very well there are probably who knows how many (10,20 50,100?) that had to give up and your not hearing from them here.
I know a man personally who started in 2004. he now has 3 trucks on the road 2 are 4 man crews and one 2 man. Half his guys are pill heads and get laid off at the end of summer. He still works with them. pays his wife to do the books. we don't talk very personal finance but I know he is grossing over 20k a month. HE just told me he is tired of it and wants out. he's sick of his employees and his customers. But he doesn't have a job to go to. He used to be some sort of tech guy but no one is hiring.
A lot of very successful lawn companies had something else going for them. one of the best in my area had almost unlimited outside funds so his business was built from the very best from day one. and he had a lot of connections to get commercial accounts. rich parents.
Another of the most successful already owned a commercial contracting business that his father built for him. His fathers connections and money made him a very nice lawn business to go with his contracting business.
Both those guys tell every one they did it all by themselves. those in the know , know other wise
So after all that. I would say that some of the success you see in the field was not just because " the owner was soooo good". And you are not seeing all the failure in the lawn industry. and you may be falling for a little BS. My friend who started in 2004 does a lot of false bragging but he still drives a lawn mower and gets his hands dirty fixing equipment when ever he can to save a buck.
quit 58k plus benefits to do lawns? I know 5 guys who would and I have met more than 100 lawn guys over the past 20 years who want you job. And there are probably 10 times that many just in my area that started and quit with not much of anything.
I wouldn't want your job but I'm lazy and would rather go fishing and my wife doesn't mind that much. its not always what you make but what you do with it.