"Vintage" high end gear vs new and upgrade path?


I'm pondering a couple issues that relate to each other.  Let's start with vintage vs new part.   The system is ripped straight from the 90's but was pretty much a Stereophile "A" class setup in its day.  Here it is: 

  • Rega P3 with numerous upgrades & Exact 2 cartridge (new)
  • Threshold FET10/pc phono preamp,
  • Sonic Frontiers SFT-1 => Assemblage D2D-1 ==> SFD-2 Mk3
  • Krell KBL preamp (recapped) ==> ML No. 332 amp  (recapped)
  • Maggie MGIIIa's (recent factory rebuild)
  • Music server (repurposed HP server) w/ Asus Xonar card feeding D2D-1
Issue 1:  Have >>analog<< electronics really improved much in the last 25 years?  My sense is that the lower and midrange gear is better, but does that translate to the high end?  This stuff sounds pretty damn good and I'm skeptical that I'd be able to make much improvement without spending vast sums of $$.  What would the weak link be here?

Issue 2:  Despite improvements in digital I'm also skeptical about how much real sonic improvement there has been in high end DACs, especially when it gets beyond 24b/96khz source material (system above is good up to 24/96).  I'm also skeptical about the claimed improvements from DSD over PCM, so I'm ignoring that for the time being.   Obviously connectivity, music servers, the digital audio chain and computer anything has improved greatly and is vastly cheaper than in 1995.  But how far does that actually extend to the sonics?  My sense is not so much.

At the end of the day I'm interested in any upgrade(s) that would create a real, hair-on-the-back-of-your-neck improvement without spending $10k.  But I've convinced myself that so much of what I read about would be only yield an incremental sonic improvement, and maybe even a downgrade.  I need a strategy - which might just be "leave it alone and just enjoy."  Any comments welcome, thanks.
raueda1
I also run an older amp, preamp & speakers (and it's magical), so can't advise you on newer stuff. I will say however some of the largest improvements I've made are tonearm & DAC related. Switched out my rega tonearm for an older Victor tonearm & it was a huge improvement in sound-stage definition, then switched that out to a newer Polestar, which was also an improvement. In regard to digital, I'm very happy with the new Parasound Zdac & old Pioneer stable platter combination. 
Those maggies are great i still miss mine yrs later . I ran krell on the bottom and cj tube on top with pv12 pre  it sounded killer . Still look for that airy sound . (With 2sunfires) I like it all , but with all due respect the anologue is your weakest link imo planers love a great anologue front end .Just  my opinion but i would look at room treatment,ac and interconnects and the top would be front end .
Speaking of Maggies, the Tympani line of Magneplanars is a special case. The speaker had become too expensive to manufacture to allow Magnepan to continue offering it without raising the speakers retail price above either A: what they wanted to (to keep their image as a value-orientated company), or B: what they thought the market would bear. They reportedly have admitted that the Tympani T-IVa was (actually, is---they are available used, and can still be repaired by Magnepan) superior to any of their current models, even the $14,000 MG 20.7. The cost to manufacture a Tympani model Magneplanar (three 16" X 72" panels hinged together per speaker) now would require Magnepan to price the speaker above what they are willing to, for the above reasons.
Go for it my friend.
I'm on your side.....
Now I'll tell you how to max out your analogue front end to give you better sound than most of the high-end crowd can even dream of.
Don't get the Rega arm but take boxer's advice and get a good vintage arm with removable headshell like the Victor he mentions or the Micro Seiki MA-505.
Then you get the Yamamoto carbon fibre headshell (direct from Yamamoto in Japan).
Then you get a used Shure V15/III from HiFiDo for about $230 (don't bother about the condition of the stylus).
Then you get a Jico SAS direct from Jico in Japan and insert it into the Shure.
Then my friend, you sit back and listen to sounds that you've never heard before......😎