Is advice from a constant upgrader to be avoided

@mid-fi-crisis, I haven't read this entire thread but I really like your question! In response, I would say it makes sense to read and consider what virtually every contributor has to offer on forums like this. Keep in mind, however, that every opinion should be treated, as such, and the only thing that truly matters is your own ears and what you like.

I think I'm solidly in the non-flipper camp. I fell in love with music in the late 50's. Someone bought me a cheap tabletop record player, back then, to play my budding collection of 45's. If I wasn't wearing that thing out, I was playing my 45's and, later, my LP's, on my parents' Grundig console. It wasn't until 1972 that I took my first plunge into audiophilia. Before that, whatever money I had went into fast cars, 8 track players, cheap home music systems and  college. With regard to core or major components, since 1972 I've had 2 receivers, 1 integrated amp, 2 turntables, 2 CD players and 4 pairs of speakers. I've always been a two channel audiophile. Of course, I've had a bunch of other doodads like cartridges, record brushes & stuff like that. However, I tend to be the kind of audiophile that does lots of reading & research and applies whatever audiophile skills I think I've learned along the way to however much critical listening I can do, prior to a major purchase. I have no way of knowing this but I suspect flippers, so to speak, are, primarily, folks who buy without critical listening seesions in a shop(s) and that is perfectly OK.  Good audiophile shops are increasingly hard to come by, these days, and some folks have no alternative. Some also just prefer to do things that way and, again, that's just fine. In the final analysis, with most stuff, you really never know what it's going to really sound like until you get it under your own roof. With just a little audiophile know-how, however, you can make a pretty good educated guess.

I think most folks on forums like this are well-intentioned and genuinely do want to help their fellow audiophiles and/or lovers of music. However, I think there is also a small minority who are probably just plain BS'ers, folks who don't own or have never owned the equipment they say they have because they love audiophile equipment and just like to wax audiophile. That's OK, too, as far as I'm concerned. Those folks tend to come from the perspetive of what they've read or researched about various components and not always from the perspective of what they've actually heard in critical listening sesions. There are others, also, who are just wedded to their beloved equipment, specific equipment brands and their personal opinions and just dismiss everything else, whether they've actually owned it & heard it or not. These folks are usually easy to spot. Personally, I tend to put more stock in the opinions of folks who've actually owned the equipment they are talking or wrting about or done a fair amount of critical listening to those components under relatively controlled conditions. These folks tend to be much more honest and more even-handed with their "constructive" criticism. Even the learned opinions or conclusions of respected professional reviewers are, in essence, opinions and the only ones that really count are yours.

If I had been a wealthier person, over the years, or more inclined to spend whatever disposable cash I had at any given time on flipping or upgrading more audio components, I probably would have done more of that. However, I sincerely doubt I would have taken it to the extremes some folks seem to have. I think some folks fail to consider the listening environment or the sound room an audio system is going to be in. In other words, you can only achieve so much fidelity in a dorm room or a small living room. Spending more money on components can and will, often times, get you different sound in some rooms but not necessarily "better". If I were in the 1 or even the 3 percent, I'm sure I'd have a home with a dedicated sound room and have a trusted audiophile consultant(s) set up various systems in that room until I achieved the fidelity I was after. After that, I'm pretty sure I'd spend a considerable amount of time just enjoying my tunes before doing any more tinkerring. But, that's just me. Vive la difference!