You are one lucky person! (If not not a great advert for Naim’s ‘upgrade path leading people ever “upwards” and providing the revenue to maintain services and development!)
If I had stayed with my system from 20 years ago would I be happy with it now? Cambridge Audio CD2. Thorens TD150/Rega RB300/AT OC7. Musical Fidelity Preamp 2A. Musical Fidelity P170. IMF RSPM speakers. I was very happy with it, and would be happy is that was “all I had today, except that at some point I’d have ripped my LPs to make CDs and sold off the TT.
However the Cambridge CD2 started playing up about then, and within a year or two I had to replace it: Shearne Phase 7. Then the MF Pre went into oscillation on its moving coil input when playing Deep Purple at high volume, and took out a bass driver. Driver replaced, but I didn’t trust the pre after that so got a McLaren PA10. Then the Shearne started dying after 10 years (that seems to have been the life of the mechanics of a CD player, in both cases mechanisms no longer being available) - seeking a replacement for that took me into streaming.
Next I started thinking about my ancient IMFs, for which most drivers are only available secondhand, and sometimes expensive, and wondered about vpbuilding mupy own - a bit of fun DIY. Bought some drivers, but crossover is more of a challenge, untill I thought of doing active, so I bought a cheap digital XO, and picked up another MF P170 for next to nothing on eBay, and a P270 for not much more. Of course, while the project progressed, and stalled, several times, the 270 replaced the old 170 as main system amp.
Next was part of discovering digital playing post-CD, when I found that the Hugo DAC made a remarkable improvement to the sound of ND5XS - and digital became incredibly lifelike, such a step up, then neding a new NAS because the first had got was too noisy, and a bit ‘clunky’ in operation, a zero cost change inolved replacing the ND5XS and NAS with a Mac Mini running Audirvana.
That would have been it apart from the DIY speaker project that was on hold, but an inheritance gave me the opportunity to do something radical to remember the person who introduced me to music, so. Swapped Hugo for Dave, and the IMFs for PMC IB1is.
Dave has one very annoying property, which is a a very loud pop when powered on/off, normally prevented by a relay delay. But although warned about it, one day early on I was raarranging things and did it wrong - very loud noise, and a damaged midrange unit.
Final stage coming: at that point I had a brainwave: why not ipuse the mid/treble satellite units I had made as part of the speaker project, and triamp? So I tried that and liked it. But one bad thing: the three MF power amps run very hot - possibly unstably so in the long term in the cupboard in which housed, and they use a lot of electricity. Then a chance spotting of a Bryston amp going at a good price on eBay, with no bids (possibly because mis-spelt!) got me that, and I liked its improvement overvthe P270, do watched for alternatives for the two smaller MFs, and eventually one came up at a good price.
So that is it. Apart from playing with my DIY speaker project when I get time (if successful in getting them as good or better I’ll sell the EBs, otherwise give up on them (the bass end)). And the only othervthing is Audirvana has poor library handling, so one day will be replaced. Otherwise no other upgrades until something dies, which I hope wiill be a decade or two…
As you can see, many of my changes have been prompted by something, rather than being gratuitous. As I said early in this thread, answering the OP’s question: “Yes (sort of). …And I first stopped about 30 years ago”!