If I was starting over, with today's tech at today's prices, with my current knowledge...

I would still go with a Nikon DSLR system for the ergonomics of the camera bodies.
Still go with a physically large camera body for my large hands.
Still start with the consumer-grade lenses as they make a great "family vacation" kit in addition to my "professional photography" kit of f/2.8 zooms.
I would skip the DX cameras as the FX cameras do better for me based on my old film SLR habits and thinking, as well having as better high ISO handling for low-light sports.

I would've assisted more.  I would've gotten an education in business.  Actually, I would've picked any other profession than photography.

I'm happy with the way I went, buying successfully better gear as my interest/knowledge/skillset increased.

I would take classes though if starting over just to make the learning curve that much shorter.

If I had to start over right now using current knowledge, I'd buy an iphone and just post pics with that.

According to the internet, potato pics are fine. No point in wasting time money and effort trying to take good pictures. Horribly out of focus, poorly exposed pictures are the new normal.

I read it on the internet, it must be true.

I wouldn't change much.  I learned from my father, so no changes there.  And I've been using Nikon equipment for more than 30 years with no regrets.

I did miss out on one opportunity, though. When I was in college, I did a favor for a buddy of mine, who was the sports editor of the college paper.  They were short handed at the time so I helped them out by taking some pictures of the intramural playoffs.  The editor of the paper like them so much, that he offered me a job as the paper's sports photographer. But I turned it down because I thought it might interfere with my drinking and partying (and it would have, too   ).  

In hindsight, I should have taken that job, at least for a while.  Nothing will make you a better photographer, than the pressure of having to come up with good pictures (especially back in the film days).  It forces you to think more about your photography, and to plan things out.  As a hobbyist, if I screw up a shot, it doesn't matter.

Truth.

What I need to do different is quit using the spray and pray method when using digital.  I need to pay more attention to my exposure and composition, so I don't have to sort through 25 or more pictures and choose the best.  Digital has made me lazy.

Starting fresh? I'd stay with the Nikon lineup but buy 1 generation old pro level equipment. A d3s lightly used is a KILLER bargain yet is still upper tier performance wise. A couple of pro autofocus lens and a bunch of older manual focus glass. See the real hidden value of Nikon is their mount. It really hasn't changed over the years and is such that 30-40 year old lens still fit and work just fine and cost almost nothing.

I'd also take some classes. An intro class from gets you basics. More specialized 2-5 day classes then for the areas that interest me. I'd make a special effort to master flash but most especially I'd teach myself to SEE in terms of light. Hard to explain but at some point you can look at something and notice how the light falls on it, the shadows and the objects textures. And more importantly you can see the potiential that changing the light can have.