Brian, I don't presume to have any conclusive answers but I've personally done well with having formal professional training and education and working my tail off. I'm both a cpa and an attorney, and also an entrepreneur, having co-founded a successful internet related business that grew to over $100M in sales in five years. There was certainly a large does of luck involved in that success (there always is, more than most people will admit) but there was an even larger dose of plain old hard work. As in, 14-16 hour work days, six and seven days a week. In five years of running my company I took a total of two days off - two (and those were half days). I know that sounds pathetic, and it certainly isn't admirable but that's what it took to keep things organized and on track. Before co-founding that company I was in professional services as a cpa with Deloitte & Touche and put myself through law school at night. Again, 14-16 hour days, six and seven days a week.
My personal experience has been that if you want to get ahead financially it's a matter of getting educated, identifying and focusing on practical opportunities, and putting your heart and all your energy into it. Develop your professional skills and develop your personal skills. It seems like you enjoy mechanical things so perhaps a mechanical engineering degree is something you can pour your energies into? You'll most likely have a good paying job when you graduate with a Mech-e degree.
Net, as others have said, there's no easy path. It's kick, fight, scratch, push and shove your way forward and if you do that for enough days and weeks and months and years you eventually get there....