Hi K!
I'm not sure how you're doing from a mobility perspective (both ambulatory and vehicular), but here are some ideas:
Disclaimer(!) : I think the pursuit of perfection here could definitely be the enemy of pretty-damn-good-enough! Don't over-do things...
So, a while back when I was forced to be out of work for a while, I was hating everything that normally gave me joy. Listening to CDs (I started collecting music just as CDs were becoming the norm, so I sold my Thorens TD120 & SME MkII/ortofon, and bought a CD player), pottering around in the garage, playing with car audio components, etc.
One day, as I turned the corner in my living room to climb the stairs, I thought "man, I'm passing my sound system every time I go upstairs.. what if I started RIP'ing all my CDs to hard drive?" At the time I had a "HTPC" (Home Theater PC), but any computer with a CD/DVD player would do. Remember the "Perfection being the enemy"... you COULD go nuts on a high-end DAC/ADC and set up a "real system" to capture your vinyl tunes... but we're looking for quick and easy "wins" here, right?! Imagine the sheer horro of (shudder) using one of those el-cheapo turntables with USB out?! Maybe experiment with one of those if you're wanting to try this with your vinyl collection, too.
I set the PC up to automatically RIP CDs to Hard Drive any time a new disk was inserted, and as I passed the system to go up/downstairs, I would change the disk out. I only had a few hundred CDs... so after a week or so of doing this, I had converted my entire library to Lossless music files. BTW - the PC automagically reached out on the interweb & downloaded thumbnails of the jacket artwork, song lists, etc.
THEN I had a hard drive full of all the music I once loved. I duplicated onto recordable DVDs so I could play my entire library in my car (before vehicles had USB connectors!), and more recently, copied to USB thumb drives, my phone, etc. Now I just plug the USB drive into whatever device I am using as a DAC, and I can go through my music list by Artist, or Genre, or whatever I want. I have my library in my car, my HT system, my bedroom system, ... it's with me wherever I am on my phone, etc. and YES, you could go nuts with online services, but it doesn't involve you as much as "re-rolling your own"!
After a few years of being "off" my music, now I love it again... if I hear a snippet of a song somewhere, or find myself "singing" in the shower (insurance problem right there... I crack tiles!), I can do a quick search, pull it right up, and listen on my system. It really has brought some of the joy of listening back.
Now, a bit about the whole "perfection being the enemy of "nice" enough"..."
Yes, there is space to get wrapped around the axle about every... single... detail in this process. What CD drive does the PC have, what CODEC to use, what USB drive(?!-don't get me started) to use, what DAC to play it back on, what cables to connect to your system....
For now, my advice would be "don't sweat the small stuff". Asides from the significant medical challenges you have, part of the loss of interest COULD be due to "the process" you associate with listen to your music so it's "just right". My whole-hearted, best intended advice is to let a little of that go, make it easy to participate in one of the true joys of life... then when you get your mojo back, sit back and critique your makeshift "Digital Jukebox".
I sincerely wish you all the very best as you work on getting "on the road again"/"back in the saddle", ...
Russ