As a teenage music lover I didn't know anybody with enough money to own hifi but my Mum had a radiogram and I got a mono valve tape recorder for concerts and mucking about.
When I left home to start my apprenticeship I was desperate to have something to play my LPs on and I bought a Garrard SL75 chassis when I had saved enough. In my ignorance I didn't know the deck wouldn't have a cartridge and could only afford a ceramic one, which was just as well since wired in mono I could connect it to the microphone input of my tape recorder and have music. My first system
Next I built a Heathkit amp and built a pair of Wharfedale 8" RS/DDs into cabinets and I had stereo.
These were my speakers for my apprenticeship and first 2 years at Uni when I saved up for KEFkit 3s which I put into the biggest recommended cabinet.
I had these until my first proper job and then I bought some used Monitor Audio MA3s which were fantastic, fast and dynamic with non-boomy bass.
Following loads of adulation in the hifi press I decided Spendor BC1s would be my next speaker and found my nearest dealer, Paul Green in Bath. I went to have a listen and was massively disappointed. They were fantastic on speech and lightweight stuff but failed completely on orchestral music with lots of dynamics, and as I was a huge Mahler fan so they were useless to me. I ended up with Nightingale NM Point 5s which sounded so much better on Mahler than the Spendors it was funny.
Next came Yamaha NS1000s which I had heard before but couldn't afford at the time. I still have them and they are not for sale.
I had a good rise at work and saved up for some Sonus Faber Extremas which I enjoyed for a few years.
All these speakers had been bought from Paul over the years but the next step was in the USA. I went to Akron for a meeting with Goodyear Racing. One of the engineers was a brother hifi enthusiast who took me to his dealer who had Apogees on demo. I was bowled over and since they were much less expensive in the USA and the Akron dealer offered a discount I bought active Divas with the DAX crossover and had them shipped by the company who shipped or racing cars and spares.
These were enjoyed for quite a few years but another rise in pay got me onto a "get my final speakers" quest. I was in no rush so listened to everything I could for a couple of years. I had been hugely impressed by the Wilson Watt so a baseline was the Watt/Puppy initially (This was mid 90s). The (then) French Wilson importer was actually building a special room for the Wilson Grand Slamms which were coming, but before that the set of WAMMs he had supplied to a client were coming back to him for sale secondhand. Since they were said by many to be the best available I made an appointment to hear them. They were impressive but not as special as I was expecting and horrendously ugly. He was also the Goldmund distributor and had both Analog and Apologue on demo. I had never heard Goldmund speakers, and the brand was not much talked about in the UK but hearing them was a revelation. The musical timbre was the most natural I had ever heard and the bass was so natural, something really rare IME. It was a bit of a surprise.
The dealer told me Goldmund was about to replace the current range with the modular Epilog speakers so I arranged a comparison between the Epilogs and the B&W Nautilus which I love the styling of and had a splendid reputation too. This was my final compare. There was very little in it sound wise but the Epilog 1 only required one stereo amp and the Nautilus four, which meant with amps to do the Nautilus justice it was quite a lot more expensive so the Epilogs became my "final speakers" I added the Epilog 2 bass modules as soon as available and have had them for 20 years now.
Despite them being my "final speakers" I became intrigued by horns a couple of years ago and after listening to a few ended up buying a pair of Tune Audio Animas 2 years ago as well.
The last extravagance has been a pair of Devialet Phantoms which I consider superb value. I suspect if I had only come across Devialet in the last couple of years I wouldn't have paid any attention, since their web site and marketing are buttock-clenchingly embarrassing, but I actually came across them over 5 years ago before the LVMH investment when they were a tech company and, as an engineer, have been impressed by all their products.