Thank you all for your wonderful thoughts so far on the subject. It's perfect reading material for my sacred saturday morning coffee. There's too much great input to address individually, so I'll put some of them together into shorter sentences or ideas as they pertain to me personally. I'm also generally interested in the subject, so there's no need for everything to apply to me as an individual!
I love that this forum is an old-timer's forum. In my everyday life, at 30, I'm an adult. "Unc", as my youngest colleagues and acquaintances call me. But there are many people on here who have been playing for much, much longer than I've even been alive. By this community's standards, I'm quite inexperienced. It's always a treat to be the rookie, because you're the one that gets the most learning material.
To put it bluntly, I look up to a great many of you and consider you great thinkers within the world of guitar. I truly appreciate the community.
There are many great perspectives and thoughts already, and I take them to heart. One thing I specifically am more open to after reading this thread, is acquiring a big hollowbody. I've always dreamed of having a giant jazz box, even if it's almost purely an aesthetic dream. I haven't tried many to live up to what I imagine, though I'm sure it's out there. Someone in my little town, unbelievably, was selling an all-solid wood archtop quite recently for a price I could afford, but regrettably, the ad has been deleted. Even if it wasn't sold, I don't have the guy's information.
At least I can have my eyes and mind open to it. I'll at least travel to see a guitar, though I need it to be all-solid I think.
Below are some answers or extended thoughts to specific points, and some direct answers to specific questions.
I look forward to the continued conversation.
1: "You should try X guitar and amp and/or have a collection"
- This is why I wanted to give the context of my personal experience(s), to indicate that I've tried almost everything under the sun, at least at the point at which I lost interest. I started out on Stratocasters, but these days I simply don't enjoy playing them. What I consider my best session was done on two different stratocasters as I recall (one was a superior instrument and sonically, though the other had a spectacular top register that was needed for the end of my part), although I'm happy with the result, the process felt like a fight between the instrument and myself. I've tried several different boutique strats (James Tyler being my favourite), average strats, and vintage strats. They all feel like obstacles to me.
2: "What about your amplifier and pedal setup?"
- I completely forgot to mention that I play digitally these days, so in my mind I have access to the entire world of guitar equipment. Some will disagree on the quality of digital signal chains, but I personally have sold everything as I find the digital setup sounds exactly the same as my old setup(s) miked up. Heck, even using some clever impulse responses to get more of a "room" sound, it can sound like you're playing an amp in a room.
Before then, I used to mainly play a DV Mark Jazz 12, which is an excellent amplifier and takes pedals well. Prior to that, I had a bunch of different amps both valve and solid state. I can't name a single one where I felt that it had -the- sound, as I was mainly looking for a fairly neutral amp that took pedals well so that I may shape the sound to my needs.
3: "Maybe you should try taking a break and/or playing acoustic only?"
- I believe in this suggestion, but, it's something I already do. I play electric guitar quite rarely these days, but I play acoustic a few times a week. In addition, I have frequent work trips that are week-long, and I might not touch the guitar for a week after that trip too. I truly believe in taking breaks, but it's not made a difference to my particular problem. It has, however made me a much better player, as I find that my playing is the least stale it's ever been.
And lastly, some specific answers.
@garybaldy: Here is a link to a picture if you're curious.
https://i.imgur.com/A3Aprbt.png
@Jimmy Mack: That's an excellent idea to "go back". I can't think of any endeavour which isn't improved by going more in-depth with its history. I fell into the fusion pot when I was quite early in my interest in jazz guitar, so I have undoubtedly both skipped and missed a lot of critical guitar history. I almost think I shouldn't mention it, but I've never even listened to a Johnny Smith record.
@Woody Sound: The ES-139 was a very short-lived and cheap "Guitar Center Exclusive" that must have sold like crap, because several found their way to Norway where I live. It is a 339 body with a Les Paul-style cutaway and chambered centerblock. It originally had Burstbucker pickups.
I studied at a school which has been through mergers many times, and today is an institute within Kristiania University College in Oslo. I chose it because I still think it's a great school to go to to learn how to actually be a professional musician, even if it's ridiculously easy to complete your degree there. It doesn't have any degree of creative weight (though the professors are at a high level) because of its orientation toward the professional, as in, if you play Taylor Swift-guitar you could get an A because you nailed that expression, and if you're a jazz guitarist you can get a B because you played a couple of clams on Giant Steps, if that makes sense as an example. I do think it's a valid way to evaluate a professionally oriented education, but it means that it's not like say, Berklee, where if someone tells me they studied there I'll automatically assume they can play circles around me. If someone went to the school I went to, I'll assume they can't play an extended chord, but they might be great tour managers...!
@mr. beaumont: Solo guitar is the bulk of what I do. I have a 7-string classical guitar that to me, feels like playing a really great grand piano. It makes my other guitars feel like toys, it's a fabulous instrument. I do think you're onto something as regards the true culprit, but I've been feeling unusually comfortable with my playing style lately. I've felt that I'm in-time and creative, as opposed to mechanical.
Guitar Amps built into case?
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