Very interesting question. I also go for older kit, especially speakers, but amps too - and some of that is just because I think they look cool!
My own personal belief is that technology in the middle of the sound reproduction chain has developed almost beyond recognition (sources, transports, amps with class d, etc), whilst at each end (by which I mean recording and speakers) it either hasn’t moved that much or indeed gone backwards.
Examples of this would be that Kind of Blue is still one of my reference points for exemplary recording and production, it just sounds fantastic and I can’t imagine how it could sound much better! Whereas modern digital recording technology, tastes and techniques often just sound horrible to me - even if it is ‘technically’ amazing.
And with speakers, OK so manufacturing processes, materials and tolerances etc have all improved a lot and we now have computer modelling and tuning. But the basic physics and technology is still the same - so I’ve no doubt that there are some amazing modern speakers out there - but a good pair of older speakers will me most of the way there - and get me that nostalgic fix to boot!
So for me - I use the latest tech with regard to source (always messing around with Pi boxes and dacs - and always hidden out of sight as it looks horrible), amplification is either vintage or modern but basically ‘old-school’ tech (preference for class a/b) and my ‘newest’ speakers are early ‘90’s, IMO sound pretty good and look great!