I came of age as vinyl was dying. I never bought an LP in my youth. I bought cassettes, then CDs in late high school, college. Then SACDs (remember those?) after that. Then I eventually ripped all my digital media to a NAS and now all of my digital listening is via streaming, either from my own FLACs or Tidal via Roon.
I got into vinyl late, like around 2011-2012. My first turntable was a Project Debut Carbon with Ortofon 2M Red. It definitely had its limits, but it was enough to let me enjoy LPs.
My turntable is now a restored Michell Gyro SE Mk II, refurbished and brought up to present specs, and upgraded with better, modern materials, like PTFE washers, ceramic ball bearings in the spring towers, DC motor, etc.
Tonearm is a Jelco SA-750D with VTA on the fly mod. Cartridges are a Nagaoka MP-500 (MI) and Audio Technica AT33 Mono (MC). My LP collection, ~400ish, is exclusively jazz from the post microgroove / pre-CD era, i.e. things that were originally issued on LP.
(I also had the much ballyhooed Denon DL-103 for a while until my house cleaner broke the stylus. Despite its cult status, it never sounded better than my MP-500).
I'm a bit of a heretic in that I'm using the DSP-based phono stage of the Devialet 400. Some will moan and cry about this being a digital conversion, but the RIAA implementation is much better than any analog stage phono I've ever heard, even at stupid high prices.
John Atkinson in Stereophile also agreed that it is a very very good implementation.
In no way do I think my vinyl collection is objectively superior to my high resolution digital collection.
However, I like vinyl for the followings reasons:
1. Collecting LPs is much more fun than accumulating digital files
2. My best LPs can be musically engaging in a way that is different than digital. I suspect this is due to euphonic distortion and amplifications of resonances and room feedback that can make things seem more lively, dynamic, and 'in the room', as opposed to listening to a recording from another location.
3. It fulfills a need to tweak and fiddle with stuff. I feel less foolish dorking around with turntable optimization (which is actually a real issue) than getting involved in silly digital snake oil fetishes.
4. The Gyro SE is mesmerizing to watch in action:
5. Experimenting with different cartridges is a fun way to play with the system sound and very real (they're transducers), unlike fantasies around speaker cables and USB scrubbers
6. Investment -- okay, nothing to retire on, but my LP collection is now worth more than I paid for it, and I get the fun of upgrading to better, rarer versions of albums, or comparing different versions / pressings / issues of the same recording.
7. As mentioned above, for some reason enjoyment increases more with decreasing sobriety than with digital
Downsides:
1. The higher end, better sounding, more sophisticated stylus shapes are a complete PITA to get really dialed in. Aligning a .12 mil (Microline / Microridge) to .26-.28 mil (Shibata, Fine Line) stylus is timely, and frustrating.
2. There is no perfect alignment. Stephenson, Baerwald, Lofgren....they're all comprimises and you will have portions of an LP that are measurably higher distortion than other parts.
3. Arm / cart matching is critical. Until I got a super flexible arm like the Jelco, I had no idea of just how many variables one must take into consideration (compliance, effective mass, resonant frequency, damping, headshell weight, etc.).
4. Realizing that there is no point in pursuing ultimate perfection -- if you want that, listen to digital. And, yet, the resist to upgrade persists. A paradox.
5. Wasting hundreds of dollars in cartridge accidents / mishaps / maids / cats
6. Sometimes I'm just too damn lazy to go through the LP ritual
7. Liking vinyl sometimes means being associated with ignorant mouth breathers who spout nonsense about analog's "unlimited sample rates" or other anti-digital garbage
8. Buying bad LPs from bad, semi-bootleg labels that are just CDs made into LPs, instead of being remastered for LPs
9. Scratching or otherwise damaging LPs