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

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.

My own journey started with a modestly priced Athena TT produced by SRM Tech in the UK a small 1 man band maker of rather nice TTs ..with a Graham Slee Gran Amp 2 phono stage and Cyrus 6XP amp running through KEF LS50s ...which sounded as good as i remembered from my teens  ...after a few years i got the urge to upgrade and started to look online ....its taken 5 years of patiently waiting to pick up at prices in my budget ....read 2nd hand ...from the bay and forum members sales ....so now i have what will last me ....Atmo Sfera TT ...with Ortofon Quintet Black S stylus got at 1/3rd original retail... a retired dealers personal TT, a Pathos in The Groove Phono (as i needed MC phono) at 2/3rds of retail as open box, Minute EL34 amp (by SAC) at 50% retail as i really wanted to try a tube amp and to round off the system i found some Klipsch Quartets for a good UK price again from a retired dealer and boy does this system sing with both my teenage albums from the 70s and AP/Mofi etc new records ....my point of this is to say that the Athena TT & GS phono cost around £500, i already had the Cyrus & KEFs... and the current set up cost about £2500 all in over 5 years so around £500 a year, taking my time picking up things as i've come across them with a goal in mind ...the journey is all part of the fun in this hobby