I hear you. I have a Victor TT 71 drive in a Victor CL-2P plinth with two tonearms, Audio research SP8MKII, McIntosh MC40 monoblocks and Altec Valencias. I couldn't be happier. It would take a lot of money to beat this system.
I'm pretty certain that the best system from 1960 would sound great today.
Same goes for every decade since then.
The bigger improvements I think are to be found in modest entry level gear.
My first 80s system Rega 3, NAD 3020, and AR bookshelf speakers would be easily bettered by today's Rega 3 and any NAD amp backed by something like the Q Acoustics 3030 (nevermind the KEF LS50s).
The fact that some 30+ year old stuff can sound so good is also a testament to its build quality.
Come to think of it, my speakers, the Tannoy Berkeley's, are 40+ years old (give or take a complete recone and a crossover update in 2014).
I even know someone who's using original JBL l100s which might be nearing 50 years old! Again give or take the a recone or two. Apart from a slightly sharp treble output (to my ears at least) they have an amazing clarity through the mids.