Major mistakes made in assembling your audio rig

Not upgrading my speakers sooner. In my defense, they were DIY speakers that I built with my mom, so they had sentimental value.

But I was spending money on accompanying gear that would have had much more impact on the sound if it went to speakers instead.

Can honestly say I haven't made many mistakes the last decade or so.
The system sounds wonderful , I'd be hesitant to change anything.
We can always look back and say, I should have went one more step up when I upgraded this or that, but then what would we do later ?

Sorry to quibble, but I'd rather say that I am and have been learning. Reading a lot of equipment reviews, more to glean a better basic technical understanding, has helped a lot. Engaging in a lot of Forum discussions with the likes of Ralph (Atmasphere), Al (Almarg) and other techies has really advanced the ball.

But here's a gripe. My interest in audio started about 40 years ago. Back then, there were a couple of high-end retailers who welcomed (or at least seemed to welcome) me and a couple of buddies to hang out and listen to gear and shoot the breeze. Also, I don't recall there were as many equipment brands to obsess about. Maybe there really were, but there wasn't interest either.

The oracle of the day was J Gordon Holt when he ran his underground Stereophile pamphlet. If JGH said something was good, it was good. But again, what did I know? I was a kid.

Well today it's hard NOT to make a mistake. Yeah, like many, I have bought and sold gear. I thought there was method to the madness.

Right now I'm stuck on speakers. I think I'm ok with my Paradigm S8s, but there's some other brands I'd like to check out. The thought of buying and trying and then ditching and trying again is a non-starter. My wife would skin me alive and frankly I don't have the energy. And like others have said, there just not that many high-end B&M stores around anymore, and for the one or two that might have some of the gear I am interested in, I am not comfortable "hanging out" like I did 40 years ago.

Bottom line: to call my progression a series of mistakes is harsh. It's more a steady process of figuring out what works and what doesn't, and the reasons why.

Nice post; I agree with your take on the subject and feel that I am in the same boat. Some thoughts that come to mind:

I think that it is true that "back in the day" there seemed to be fewer choices, and many of those choices seemed to be able to tap into and give us that elusive quality that some of us refer to as musicality (like the sound of live; or, at least, having a good dose of it). I think that part of the reason for this was, ironically, because of the very limitations of the equipment. Contrary to what some fans of vintage equipment feel, I think that, overall, today's gear is infinitely better. The problem and irony are that as gear has become "better" (more transparent to the source) it also becomes easier and easier to put together a system that sounds poor (unlike the sound of live). However, it also becomes possible to put together a system that is far better than anything that I heard back in the day if one is willing to devote the time and research and deal with the inevitable mistakes? Not easy, considering just how many choices there are. Personally, I try not to stray too far away from the approach to system building that made it so much fun back then.

Having a $1k phono cartridge within reach of a 2 year old.
More of a parenting mistake than an audio mistake, but it still hurt...a lot.