If you had to do it all over again, would you do anything different when you started gaming?
Looking back, I don't know if there's really anything I would have done different gaming wise. I've had a great (around) 20 years of playing!
I only have a few minor regrets. I wish I wouldn't have let religion make me think that I was doing something wrong. Not that I ever bought into the D&D is Satanic, but I did have the mindset that it was distracting me from godly things when I was younger. I also wish I didn't have the "not playing that edition so I should sell it mentality that I used to have.
I'm looking forward to the next 20+ years of gaming. I know they'll be some good times.