I have had modern equipment such as Musical Design amps and pre, Adcom, Lazarus H1-A hybrid amp, platinum audio, Mission, Odyssey Loreleis Quad ESL-63's, Pinnacle Classic Gold Aerogels, Tannoy DMT12's and others..
Currently my main rig is a pair of early 1980's David Berning's EA-230's and his TF-10 preamp.
Vintage wise I have a McIntosh MC250, Scott 299, Fisher 400, Allen organ amp (6L6), Allied tube amp and tuner, and a Scott LT-10 tuner as well.
I find myself lately listening to the vintage stuff hooked up to Tannoy Monitor Gold 12's or EV12trxb's...Especially with the Scott, I dont find the difference to be that tremendous...Only my Berning amps seem to be a bit in a different league. I have found the same relationship either with vintage or modern speakers.
I think that if the vintage equipment is up to spec, the differences will not be that great, especially in tube gear. SS may be different. I do have a Pioneer SX-850 and I just dont find its sound that engaging.
To me there is something special about having vintage gear with beautiful walnut cases..a treat to the eyes and the ears.