What I wish I knew before starting my audiophile journey

Path OP followed is legit path, lots of churn, but with internet marketplaces this is much easier than path I had to follow pre internet.

My pathway was first determining sound quality I was trying to replicate at home, for this I listened to a wide variety of home, dealer and audio show systems, this over many years. I'd pursue systems rather than concentrating on individual components, in other words research individual components I thought would be sympathetic to rest of system. I'd gradually build up systems to a conclusion, at which point I'd sell off virtually all components and start anew when negative conclusions were reached. Negative conclusions fell into one of two categories, excessively analytical or romantic, conclusions were drawn by a slowly dawning truth that only  certain types of recordings were being played over and over. I'd play recordings that sounded poorly and blame the recordings, over time not being able to play a wide variety of recordings was untenable, back to drawing board. Once I got past excesses on both ends, neutrality was adhered to in component purchases, this has been much more pleasant experience. Can be difficult to achieve this, but tweaking and tuning can play large role if one starts with neutral components to begin with. Tuning and tweaking is steep learning curve, but much research and experience helps one get there. Listening is key to both, learn WHO to listen to, comparative reviews from experienced reviewers, context in the sense of knowing the reviewer's  components and their implementation into a whole system will help to determine if the items under review will work in your system. And then we need to learn HOW to listen, WHAT to listen for, experience listening to wide variety of systems helpful here.

Over time if there's  one thing I learned, it was to start off  building systems with sympathetic partnering of amp and speakers, getting this wrong will ensure you'll never get to positive conclusion. This assuming one has AC and room in order, those two are prerequisites.

@chriszponder Good to hear your son recovering!

I hear you on how expenditures on audio system can overwhelm our finances. I always tried to stick to rules of not buying anything on credit, having to sell something, didn't need to be audio related, to help in purchasing new additions. This has worked out pretty well for me, can't say the same about motorcycles and cars!

I also believe the Equi-tech is all you'll need. I have BPT, another balanced transformer based conditioner. Previously owned earlier iterations of PS Audio power plants, they went away, BPT far superior. I transferred one of my PS Audio to home theater system, provides good service there.

I agree highly unlikely someone's going to optimize AC and room prior to any hardware purchases. One's necessarily going to start with amp, speakers and source, assuming one hasn't paid attention to room and AC, they're  likely to begin the churn, always blaming the equipment, ignorant of how large a contribution AC and room bring.

@waytoomuchstuff Interesting to hear a dealer's perspective on this, I often assume others as attentive to small details as I am.

I've also run in motorcycle and car circles nearly all my life, seems like I'm always around OCD type people! Can't recall meeting another audiophile, motorcycle and car nut in one package.

@tonywinga Estimation of audio journey and tiers of audio very well stated! Audio just like nearly all human endeavors in that complexity nearly always in upwards trajectory. Questions never end, answers are discovered. The one thing I'd add to the upper tiers is the many paths available within those tiers, for example SS or tube, high power, low efficiency speakers, low power, high efficiency speakers, and then we have variations within these paths such as Class A, A/B, and now D for SS, SET and push pull for tube. All these paths can have great variations in cost to reach the highest tiers, for example high power usuall means higher cost. And then we have sound preferences within those tiers, highly doubtful all would find any particular system within that tier to be satisfactory, some may even doubt it's placement within that tier.

So, we see the complications never ending, for those desiring to reach the highest tiers be prepared to enjoy the process otherwise this is all tedious and a burden. I've thought more than a few times along this journey how satisfied a normal person would have been with sound quality I had attained at certain points, in those moments doubted my will or need to reach for more. I should have been happy! In recent years I've been contemplating on the idea I'm nearly at an end in this journey, with recent parcel of purchases all things on my audio bucket list have been exhausted, nothing left on short term list and only some nebulous plan for another diy custom build streamer in the future. The question becomes are we really ever done, I'm at point I'm about to find out.