Yeah, music should be all about pleasure regardless of what skill level you're at. Sorry but if you have to wait a year much less 50 to consistently have fun, you're doing it wrong. I feel sorry for Jamey it took that long if that's really true.
Thanks to everyone who's contributed! It's much appreciated! Great to hear your experience!
I think Jamey is an unusually honest guy based on my personal dealings with him and his organization, but I suspect that he's exaggerating to make a point to put his campers at ease with that statement. I'd call that a self-effacing gesture more than anything else. He's not a perfect guy, but my interactions with him indicate that he's kind, generous, thoughtful, courageous, and intends to make the world a better place. Can't get too much better than that, IMO. One of the heros of the 20th century and how many of them are there?
As far as the criticism that he over-complicates things, I'm sympathetic but, in my educated opinion, his way is accurate and if anything, tries to address every possible situation, and so, maybe you don't need all of his theory to find your way to playing well, but that doesn't mean that Jamey's nomenclature is overly complex - it's just very thorough. The more I'm exposed to it, the more I appreciate its accuracy and SIMPLICITY, and I think that says a lot - the more I get into it, the simpler and more accurate I find it. Maybe you'd find the same thing if you spent more time with it.
In my case, I'd say that I've always loved music and have loved to play it even more since I was a young child - 6, 7 years old. To this day, one of my favorite things to do is to practice and when the band is hot and happening... better than sex - okay, not always, I've had some pretty great sex in my half-century - but in the running, anyway.
That said, for me, it kind of comes and goes. Thinking back on it, maybe as I pass through each stage, at first it's new and exciting and, ego-boosting honestly (?!?!), "I get to play with THESE guys, wow!", but that gives way to frustration more than anything as I work through that stage.
About 18 months ago I resolved to finally master my instrument - I had gotten some, what I now consider to be bad advice from a previous teacher - he had great musicianship and ears and so I accepted his advice but have come to regard it as ultimately self-defeating. Things like "don't worry about thumb position because the money notes are below D", etc. Similarly, that teacher pooh-poohed ear training and transcription while a later teacher basically said "You can't play it until you can hear" and I think I've found that the later teacher's advice works for me.
At every stage I've had fun, even at the most basic near-nut exercises with Simandl. Even back when I had to write out my bass lines because I couldn't read the changes fast enough. But that's nothing in comparison to hearing a tune solidly throughout the performance in my mind's ear, not having to worry about my intonation or the mechanics of playing the bass and getting a good tone and hearing what the other players are playing rhythmically, melodically, and harmonically, and responding to it in a, not just meaningful, but artistic way, to shape and participate in the shape of the tune as it progresses. It becomes a living artistic entity of its own and I find that extremely gratifying as I become an equal partner in the performance.
So, for me, each stage has had its fun and then its drudgery but I'm tenacious enough to work through the drudgery until it becomes fun again and each new level is an order of magnitude more rewarding than the last.
It sounds like it was easier for most of you than it was for me, but I thought I'd put it out there for folks like me, to let them know that they're not alone in their aspirations, frustrations, and doubts. I suppose the takeaway is 1) get a well-respected teacher that you feel you can trust 2) work hard to push through your weaknesses and 3) it can be worth the sacrifice - but plan out that day-job just in case.
Still giving back.