new member, some questions, need help please

Regarding your general question of whether or not speakers from 30 years ago still hold up today I can lend a perspective. I have a pair of Thiel CS6 speakers powered by a Krell KSA 300s that date from the mid 90's. I've been to 3 audio shows and I can testify that my system easily holds up to most every system I've heard under 6 figures. I've heard several systems that didn't sound as good as mine where the cables cost more than my entire rig.

I have also observed that the sound quality of speakers have become more similar relative to price. In other words, the difference between $100k speakes and $15k speakers is not as much as you would think. My overall advice is to go to an audio show or two and reconnect with the hobby. You may find that there are wonderful speaker choices that are affordable and that don't have the age related issues that older speakers could have. But if you have your heart set on a pair of WP's I don't think you will be far off the state of the art.

I didn’t think much of older speakers until I got a 20 year old and then a 40 year old. They both beat my 2 year old Evoke 20s

the difference between $100k speakes and $15k

I am pretty sure it's that last 10%

Same as between a 3K speaker and 15K speaker

Danny from GR Research has some very illuminating YouTube videos about the subject of speakers, parts and design. He has opened up some expensive speakers and often been surprised/disappointed by what he has found inside and the measurements of the speakers. It’s always good to do homework and it’s not always how much more money you spend….

I remember my first Wilson Audio experience and understand your interest. If you are on the east coast of the US then the upcoming Capital Audiofest outside of Washington DC this November is highly recommended. The WattPuppy line did seem to mature into the Sasha’s and there is improvement between the 1,2, and DAW versions though one has to consider the price differences. Your room size should also be considered. A smaller room might lead you to look at the smaller Wilson Sabrina X. An audio show would allow you some time to hear many brand and size choices, though they certainly do not represent a fully optimized setup when in a hotel room. I like the Wilson sound, but like @ronboco I love my Rockports.

I think if you can go out and listen, you will find that the Watt Puppies have been eclipsed in their price range. I audition but can't afford... I'm a window shopper when it comes to a certain price point. I settled on the used Maggie 1.7i, and am about to buy a pair of "bass" panels, but for what the majority of my listening (big band, bop, free jazz, fusion, prog rock, avante garde, experimental, jazz vocalists, and 60's psychedelic) the 1,7i has been great. Hard rockers won't be satisfied with the bass response. Don't throw out the quality cassette deck, in my world there are still artists that release primarily on cassette, and CD, and are sometimes hard to find on streaming platforms because those artists self release and there's no corporate level $$$...