Mine I guess started with my Dad - he was very much into HiFi - has a Quad 22+202 and some speakers he made himself, then a 33+303 and the original quad electrostatic speakers and the matching tuner. Somewhere along the way he also bought an Ampex valve reel to reel. Then of course he upgraded to 44pre-amp and 405 amp and again matching tuner and ESL 63 speakers and a Linn Sondek LP12 and a very nice bluepunkt cassette deck (cant remember the model) - this was back when they first came out.
This is about when my journey starts in the early 80s - Sansui A60, Sansui speakers (cant remember the model), Sansui SR222 turntable and eventually added a Sony TC-FX6C cassette deck (one of the first with Dolby C.). Shortly after I got in DJing (still early 80s) so I ended up replacing the SR222 with a technics SL1200Mk2 and along with a friend who managed to also buy one - we started DJing and HiFi took a bit of a back seat in favour of live sound etc having been sold in order to buy live sound gear and synths and Roland TR303+TR606 bass and rhythm machines.
Roll on 30 years and most of a 6.5mx5.5m 'living room' is given over to a studio full of racks and synths and the nearest I have had to any kind of consumer audio in my house was an Sony 5.1 HT system bought shortly after I got a top of the range trintron sony TV (yeh - that's how old it was). So I have basically had a diet of active studio monitoring + high end professional DAC, DJ decks (SL1210s + DJM-800 mixer and CDJ-1000Mk3) as my means of listening to other music.
Now that I in my 50s Ive finally given up DJing and production and started selling off the studio gear to make room for normal living room, (much to my wife's relief I should think

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Last year the old HT system finally went out with a bang - literally. So mad rush to find a replacement, pretty much the first thing I could find that had pre-outs, so ended up with a Yamaha AVR (RX-V781), then ended up buying some Yamaha floorstander speakers, sub + AV speakers and CA Minx Min 12 for atmos heights and we got an AV system back. While this was fine for TV/Netflix etc, not so great for activity listening to music, so went amp hunting and eventually ended up with a Yamaha A-S2100 at a discount (as store was having trouble getting an A-S1100) which I am very happy with, but was using the AVR's zone 2 out for streaming.
Kind of on impulse I signed up for a tidal trial and bought a dragonfly red dac for my iPhone (for my car and work, but also curious about MQA) and through these forum read a post about Roon one day. After looking into it I realised I actually already had all the hardware to make the most out of it - ie Raspberry PI with a touchscreen, a QNAP NAS and a USB DAC with MQA support to plug into the raspberry PI, so I signed up for a trial with that, converted my raspberry PI into a Roon player and controller and my NAS into a media and finally that all my streaming needs nicely met.
Well almost (still figuring out how to make Roon play music off my NAS and stream it over the internet to my iPhone wherever I am - car/work etc). Other than that, Im really liking Roon and being a programmer, am slowly writing a new media controller app for the Raspberry PI for it (to integrate with other home automation as well, particularly Harmony and AV + lighting control).
At some time I will get around to HiFi-izing one of my technics SL1210M5G turntables with a decent cartridge and plumb that into the Yamaha Amp (already tried it with the ortofon electro DJ cartridge and even with that it sounds excellent by vinyl standards). I probably should really get rid of the turntables as I don't really listen to vinyl very much, but I still like to mix as to me its kind of like tinkling on a piano and I literally have a shed load of 12" EPs still so I keep them around, kind of like people hang on to a musical instrument.
Next upgrade itch for me is likely to be my speakers - probably KEF R series or MA Silver series and a much better USB DAC I can leave at home and permanently plumbed it - contenders are Pro-ject S2 digital or RME ADI-2 DAC currently (as I have one of their big studio audio interfaces as well), but not really set on either as both have some use issues that I'm not entirely settled on.
Its also an adjustment for me to simply listen to music rather than trawling it for samples or inspiration or as potential set material - with the new amp I've finally got the clarity I'm used to from studio systems and with great sound it really encourages you to relax and just enjoy instead of my normal impulse to latch onto mix flaws etc
