If you had to start all over again in this day and age

Haha, OP, yeah that’s true. But I’ve been tested for the audiophile virus, and, sorry to say, I did not test negative. I’m guilty of wanting better sounding components and despite just upgrading the three systems and dropping well into five-figure land on the combined projects, I’m already thinking the bedroom system could sound a lot better if maybe I got that top Luxman integrated for my main system and moved my used circa 2010 ARC integrated to my bedroom........so yeah, I’m no pure white dress bride (ha!) in this consuming hobby (sickness?).

But it is all fun and I am enjoying it, the music and the gear.

But I can’t help sometimes thinking something that I’ve seen MillerCarbon state one way or the other several times over the last year (I’ll paraphrase): "Blessed are they who cannot hear the differences in equipment [like my wife and my kids, for example (parenthetical is mine, not his)], as for them life passes blissfully without the worries of how one’s system may be somehow deficient"

(apologies to MC if that isn’t close enough but that’s kinda what I took from your renditions)

As I type this, I’m at work. Not working, mind you, but because it’s early on a Saturday and the building is mostly empty, I can crank the budget system and listen to differences in the three (yes, it’s true) bookshelf speaker options I’ve collected and rotate thru .... just because. Audio sickness, maybe? Or is it pushing the boundaries and exploring a passion? Depends which network you watch I suppose, so to speak. My wife thinks for sure the former, I’m arguing the latter but, you know, she may have a point.

So alas, I’m not there. : )
But it’s all good. Enjoy the music, and stay safe.

Just put together a $10k system from scratch, so I guess I’ll chime in. VPI Prime, Hana SL cart, Bob’s Devices SKY20 Integrated VPI SUT, Don Sachs tube MM phonostage, Musical Fidelity M2Si integrated amp, Audioquest Rocket 11 speaker cable, Tannoy XT 8F speakers, and a set of Drop/Sennheiser HD650 headphones. Got everything brand new except the SUT, which is in mint used condition with lifetime transferable warranty. 
Will probably add a DAC, streamer, and headphone amp at some point, but pretty stoked at how well this turned out, and I haven’t even heard the Sachs phonostage yet as they are built to order. 

I once let a brother-in-law hear a $100,000 system in one of our stores.

He turned to me and said, "this doesn't have anything over my Bose system" and added, after I told him how much this system would cost; "people who buy this stuff must hate money".

.

arro, your bro-in-law did and does make a point to be considered.  If we were to 'begin again', would we have what we know now in mind?

Likely not...so a Bose 'system' would be perfectly acceptable.

We're 'victims' of our eras....and errors....*s*  It's taken all this time to get 'here' from the 'there' behind us....

I, for one, might be 'where' I am 'now', considering the $ of 'hi-end'...or just another ear budded smartphoner.....;)

The merry-go-round over the last 50+ years of multiple systems and upgrading, has gotten me to a point where I’m ‘almost’ completely satisfied with my sound. What I did not quite understand in those earlier years of changes, is that you have to find your sound first. That takes getting off your butt and listening, like going to shows and dealers before buying a damn thing. If you can’t hear the difference you’re probably lucky. Get something pretty at your price point and be done.

Patience, can be a bitch. I was too impulsive then. You know, when you have money to burn or you’re saving up hard for something specific from reviews or whatnot.

I am lucky to have finally found the sound that I love about ten years ago, and it doesn’t matter what others prefer as well. This doesn’t mean that I’m done. I still want to replace my line stage, because it’s not the best match for my other gear. So, I’m working to match the level of quality of my equipment to the sound that does it for me.

So, if I were to start over again, I would take the time to listen to all types of systems, find that sound, then go after it, and build upon it.
Kenny