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

Don't cut yourself short Kren. Music is in the ears of the beholder. Audiophilia is a sickness with much based on the "perception" of the listener. For those well healed and can spend $250,000 on a system, more power to them. Would this person be happy with a 5 or 10K system? Nope. But I'm not sure if the real added nuance of the music or the expectation that such a system has to produce $240,000 better nuance is the driving force. That last scintilla of quality higher priced stuff gives you is priceless to some. It does not mean in any form or fashion that cheaper stuff does not give joy. 
From my experience in the 35 years of selling this stuff, many told what they should be hearing from magazines, took precedence over what they actually were hearing.
The poster stating he would be happy with this Walkman is on to something. The snobbery and bs in this business is astounding easily rivaling egos found at horse and dog shows.

I'm admittedly an audio cheapskate, I just can't bring myself to spend tens of thousands on top shelf gear, but if I had all the money I spent on audio stuff over the years, chasing good sound, I would get a good TT & cartridge, and replace digital with LP's. I grew up with LP's, RTR &  cassettes, and wish I had a Mulligan, I would have just improved my analogue gear over the years and kept growing my LP collection. I use a tube integrated now, but wish I had not waited so long. 

richopp. You have taken what you think as my "intimation" wildly incorrectly. For me and to my taste, ARC sound has actually improved from yesteryear.
The best system i have ever heard was at a show in Las Vegas in 2011 or 12. It was comprised of all ARC componetry with Verity speakers.
If one is into what they perceive as "actual timbres" with a "you are there" perception, this did it for me.

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.