I could go as high as $50,000 but...I want a wonderful system that I can spend my time listening to that won’t put me to in the poor house.Wow, my first thought was that I'd like to live in your poor house...but then I started adding up the retail price of what I've managed to put together over the years, and I thought that # is not so crazy.
I've never heard a stacked Quad system but lots of folks say that they still cannot be beat for mid-range magic. So maybe you should concentrate on upgrading your electronics and your 'table, keep your speakers. If you want a new sub, I'd suggest a pair of Vandersteen 2Wqs w built in amps. They're designed for music not HT boom. Other than that, I'm only gonna mention tube gear since I've not had ss in my house for quite a while. From listening at home, Doshi, VAC and Atma-sphere come to mind for pre and amplification components. Great customer care from all three outfits; perhaps an advantage to Atma-sphere since you are also interested in RTR and the owner/designer has lots of expertise in using and rehabbing tape machines. At shows Co-incident and Allnic phono/line stages and amplifiers are always impressive. The owner/designer of Co-incident has a great reputation. I've not heard the higher end Aesthetix components, but their lower price phono stage left me unimpressed. As far as a new turn-key analog rig, I'd suggest working w Mehran from Sorasound if you want to buy new. Buying used electronics from established members on this site has always been a better-than-anticipated experience; assuming that the gorillas at UPS/Fedex are well-behaved.
One thing that has really changed in recent years is the reach of high end audio shows, to give you a chance to hear a wide range of gear and talk to and learn from many of the manufacturers/designers. Rocky Mtn Audio Fest in Denver each October is probably the biggest/best, but there are shows in DC, NYC, Newport Beach, and other places. Highly recommended.