Every house I've ever bought I've lost money on. I know there are people who make money trading houses for a living. I'm the worst at making money when it comes to houses!
You can't say for sure where you would have ended up without education. Now I'm not saying education is useless but you also have to account for the money and more importantly time spent acquiring it. If he has 50% profit sharing and let's optimistically say he makes 20% p.a., he can make a living out of it. Also, if he's that good he can attract money from other family and friends and that can add up to a nice AUM. In the end, people choose a path they're most comfortable with and later justify their decisions if choosing correctly and curse themselves if choosing poorly.
You should partner with a couple of these houseflippers on here and do Trading/Houseflipping seminars. I'm sure they have probably already Pm'd you. Keep your eyes and ears open they're a shifty bunch.
That's obviously true for almost everyone as you'll be rejected before being interviewed (I imagine). That said, you don't know what it would be like if education was ignored when hiring staff. You can't form an exclusive club and then claim "it's obviously because of our education that we've done so well". Imagine if the requirement to work in finance would be to be Chinese and the Chinese would then claim they're the best in finance.
True, for any of us. It is a hypothetical argument, for me, to tr to determine if I would have been better (or worse off) with the education, than without it, and vv for those who posses the education.
I could not imagine trading for a living having 2 kids and a mortgage unless you have a very large bankroll or a working high earning spouse & reserve cash to cover living expenses for at least a year or two. 'The only thing that interferes with my learning is my education.' - Albert Einstein
When I wrote "price it at the higher end of comps on superior homes in the neighborhood" ... I meant without any upgrades. Even if its at a 7.5 on a scale 1 to 10 presently.... price it at an 11. I realize that current banking regulations will nix any buyers at that level requiring financing as they are very stringent on appraisers... but in a city like Chicago you have a plethora of cash buyers that need something now. Anytime you buy real estate, you should always put it for sale immediately for upwards of at least 9% more than you paid... in some cities more. And NEVER use an agent in a high demand area.