What to upgrade to?

Turntable-wise, you could stay with what you have, and try an additional arm (Chris would probably be able to nicely add a new arm, or, you could change arms for one that would enable you to change cartridges by just changing head shells.)

I use a Garrard 401 that I refurbished on a plinth I made myself, with a Dynavector 501 arm. Changing cartridges is a snap. Sound quality is shockingly good, depending on the recording, of course. And, my speakers are Tannoy.

I know this is not the time to go out and audition loudspeakers, but I feel you might want to hold off on purchasing turntable/speakers until you can go hear what interests you. Or the free home trial is a good option, if not a pain in the butt. Oh, by the way, I'm in the PNW as well.

Well, best of luck to you, stay well, and good things will happen at the right time.

Regards,
Dan

Speakers: Emerald Physics makes several models of open-baffle. I LOVE my KCIIs (with WireWorld and Clarity Caps upgrades) $1999/$2999


Beyond, or in addition to, their great reviews, they are a very easy load.  Also,  great direct prices saves you money

hth

I would like to thank everyone who has participated on my thread.  There were alot of great suggestions.  I was pleasantly surprised that there were a few who has heard my speakers and know of Dale's work.  After listening last night I can reaffirm the the Intuitive Design speakers are extremely good.  
I have decided to upgrade my cartridge and see how that upgrade works before looking at anything else.  Perhaps a serious cartridge upgrade will be all that's needed.

@bobheinatz,

FYI - Soundsmith has most of their upper line cartridges on sale 25% off, https://elusivedisc.com/search?search_query=Soundsmith.  A nice benefit of Soundsmith is their ability to rebuild the cartridge to near new many times at a fraction of the new-cost, and the rebuild is a  new stylus-cantilever-suspension.  Makes those retirement $$$ go further, if the cartridge sound is to your liking.  I heard a direct comparison between their top of line Hyperion vs a Lyra Etna - same turntable & arm (VPI HW-40) and all the same electronics (CAF-2018) playing a Louis Armstrong record.  The Lyra made Louis Armstrong sound like he was playing Aspen, CO (crisp dry air) while the Hyperion sounded like he was playing in New Orleans (thick humid air).  They both sounded great, but it all comes down to your taste.  Otherwise, I own the Soundsmith Carmen and Paua, and these tend to be a bit sultry which is my preference, whereas the Sussurro and Hyperion is said to be more detailed.   The web has review of just about all their cartridges.

Good Luck, and remember, every change that you make to your system makes what is old new again, and when retired you should have more time to listen.  So, maybe if you budget/stage your 'improvements' you can keep that journey going throughout your retirement for many years to come.  

Time for one of the fantastic new $10,000+ phono cartridges. With your system you could really unlock great sound with something like an Ortofon MC Anna Diamond.
The other thing - it's sacrilegious - a great new streamer and DAC. Your budget would get you some great "analog sounding" digital gear. And with Tidal Masters or Qobuz Studio you'd have a chance to listen to everything new BEFORE buying it on vinyl. Which is the best way to do digital.