To venture back into vinyl or not,...that is the question.

No offense intended to anyone, but I must say that I have always found it perplexing, and not a little silly, when specific $ amounts are attached to a price point when all of a sudden it is “worth it” to do this or that. There are so many variables: the specific gear in question, synergy with ancillary components, expertise in set up, the particular listener’s sensitivity to and/or preference for the very real fundamental differences in the sound of each playback medium (regardless of cost). Sure, I’ve heard $4K CD players that, on balance, sound better than some $500 turntables. However, I have also heard meticulously chosen and set up $500 tt setups that I would much rather listen to than some $4K CD players in their respective systems and set up.

mijostyn,

On the contrary. The money I don't waste on vinyl goes to many romantic dinners with the significant other. See, that's how cost/benefit analysis works.

unreceivedogma,

I discount subjective opinion. But remastering of an old recording isn't a good analogy. And remasterings are hit-and-miss anyway. Even remastering of modern digital recordings. However, there is no grittiness to a digital recording. That is related to all the digital conversion myths.
(good example here)

I think that even most vinyl aficionados agree that their preference for vinyl has to do with its deficiencies and in some cases an album's original mastering (vs. CD's loudness wars). The technical advantage of digital is undeniable. Whether you prefer the deficiencies of vinyl or an individual mastering more is subjective.

For the OP, read the opinions and decide for yourself who makes more sense to you, no one can tell you what to do, you have to experience it yourself.
I started going back into the listening hobby a few years back, bought a Technics SL-1210 mk5 out of nostalgia with a Denon DL301 and a budgie phono stage, total was $1100 give or take, my Amp was a Yamaha integrated 2100S $2500 and purchased around 20 of my favorite records. The sound wasn't what I remembered, turns out the rock records I purchased new were cut out of digital and that makes a difference. At the same time got a Tidal subscription and started sending audio through a Bluetooth adapter from my phone to the Amp, sometimes sounded good sometimes not that much. Reading about dacs purchased a $300 project s2 dac and a $500 nuc computer running trial Roon subscription with Tidal, wow, the difference that made was substantial, music was detailed, clean and engaging, along that purchased a dark side of the moon original pressing $150 in mint state and when played my TT sounded different than with the digital repressing records, different than digital and also engaging. I concluded that chasing good pressings and paying that much for it wasn't practical (note I don't say it wasn't worth it, just not practical)
I decided to improve my hires digital streaming, fast forward early 2019 and several thousand $32000 more later (including new speakers and Amp too) and lots of researching, Nyquist, filters, modulators, low ripple power, room correction, my hires digital system was incredible with the convenience of exploring any music genre and listening to whatever you feel like it and something else you can listening and read about the musician, see who collaborated with, listen to his work with others and explore similar artist and genre, it is truly a different experience.Early 2019 started reading the analog section at audiogon and wanted to give analog that chance again, remember I just dropped analog in 2015 and learned about digital. Turns out to experience good analog sound as in digital it takes work and a learning curve, and of course money.Now I went down the route of vintage and modern Japanese TT, vintage and modern cartridges, tonearms, records and tubes for my phono stage, please don't forget the critical cleaning system, ultrasonic is preferred, to be honest I'm still putting pieces together and my analog is not complete (as a matter of fact I'm not playing it unless I am ready) but my preliminary testing has shown it provides a different magic to digital which indeed is alluring and desirable, I guess afterall I still have a romantic bone in my body.
My point, by all means venture back but as others pointed out it could be a long long rabbit hole. On the other hand as with digital you could get very good results with not so much investment.

I'm not there yet but I think subjectively that analog well implemented could be better in SQ than digital at least to my ears. I just wanted to share my experience with you as I am actually venturing seriously into analog.

I forgot to add, why do I think it is more practical getting good vinyl now? Than a few years ago? You have Discogs which is a good resource for excellent vintage vinyl, seems that more people have favored digital over analog and got rid of their vinyl and finally there are companies doing pressings taking care of going through a better process, direct to disc, etc, yes it is higher in price but not by much.