I'm very much in Hunter's camp, though. I really admire guys that hunkered down as kids/young adults and mastered their instrument. I was never really good at learning covers or even just being able to tell what a guitarist was doing by listening to a record. Music was a real struggle for me when I was younger. But there's a lot of good things going on now... lots of great information, lessons, etc... gear is cheap compared to 20 years ago, and the technology is really great... I have a Korg D3200, 24 tracks, digital, built-in effects and mixing automation and can burnt to CD, all for $1399... pretty amazing where we've come from.
I think in both the "success" and "regrets" thread though that I'd like to recommend a movie I just watch "The story of Anvil" or something like that. These guys were a bit of hit in the 80's and stuck it out for well over 30 years trying to make it back into the industry. Its a great documentary, and I found it pretty inspiring, so check it out.