I get it, my advice:
1. LPs:
AFTER you have your analog ’very good enough’. (i.e. my analog is ’done’). No longer thinking about any equipment except perhaps collecting a few cartridges.
IF into Jazz, so much great content exists prior to 1958, so get thee a true MONO cartridge. I highly recommend this Grado to start.
https://gradolabs.com/products/grado-prestige-mono-phono-cartridge-model-me
Elliptical, $185. User replaceable stylus $100.
I learned here, tried it, everyone who hears it here ’understands’ the benefit of less noise and more distinctness of individual instruments and voices that they hear when I compare it to any of my Stereo cartridges playing thru my system with the Preamp in Mono Mode (which I thought was ’good enough’ for many many years).
After that, you might think about a second tonearm, your pre-calibrated Mono cartridge ready to go in seconds. Then you can have some friends over for an Oscar Peterson evening. Have them bring a few of their OP LPs. Mix and match Stereo and Mono without a second thought.
I never tire of showing this (others are probably sick of it) but with help here, I ended up with 3 arms that I get to enjoy till the very end.

2. Quality of Individual Pressings (LPs and CDs)
Try to stop thinking about the individual pressings. Research, make a choice that costs what you won’t think and remember as too high. I got so many with slight warps, that I stopped buying 180 gm .... and after trying a few 45 rpm, I stopped buying them. It’s exhausting and expensive,
Get ’........ MIGHT be better’ out of your brain, enjoy the content, and how LPs with great engineering decisions, sound on your system. That’s it, done.
A ’few’ special loved content, ok, go all out, why not, I have 3 versions of one I love (some friends go beyond that).
3. CDs
Find and buy a new CD Player. Play your CDs here (near enough to me in Plainfield, NJ 07062?). I have no doubt you will change your mind about how good they can sound.
If you care about ink-black noise free backgrounds, make sure it plays SACDs. The content and recording engineering isn’t necessarily better, but it comes out of deep silence, I appreciate the ones I have, but I don’t actively collect them, just if a good price pops up, I might spend the difference, but standard CD’s are quite enjoyable here again.
Many will say get a transport and a DAC, you have a DAC, you could do that. I wanted a single unit and I don’t stream. My choice was a Sony xa5400es, lightly used. (lasers age with use not years), Sounds so good, I’m actively listening to CDs and even buying used ones. I mix LPs and CDs without a second thought.
4. Reel to Reel, well, think long and hard before you jump in.
Roberta Flack (anyone): come here, listen to my Reel to Reel versions. Mine are not great 15-1/2 IPS like my friend Rick’s two Otari’s, which are awesome, mine are prosumer 7-1/2 IPS pre-recorded, played on good but not great Teac X2000R.
Tapes are 60 years old and still sound better than my LP and CD versions. Ironically, technically, it is the noisiest format, but get it going, when the music plays, it is ’beyond involving’. I have friends over, play CD version; LP version; R2R version. Always, without exception people pick LP over Cd and Tape over LP.
Pre-recorded content is limited to that era, so think about that before you jump.
5. What else?
Get thee some friends to enjoy it all with!
Cartridges: buy a few inexpensive tools, and learn to mount/align/calibrate then yourself. Hopefully you chose, or change to tonearms with removable headshells, preferably ones that allow azimuth adjustment which allows you to get the fitting very tight first, then get azimuth ‘right’ fairly easily.