I see a lot of people switching to the new books for no other reason than "new edition smell". Our society has ingrained in us this strange idea that old things are somehow "bad". Hollywood won't let us simply enjoy classic movies on their own merits, there's always a reboot around the corner that's "new and improved" (but almost always, for everything improved, there's a lot of perfectly fine things changed for no real reason).
Sure there are outliers who stick with whatever edition they are fondest of- I have friends who reject various editions of D&D for their own reasons. But when people say "I want to get into this D&D thing", they're going to buy the books that are being sold. They're going to assume "newest version = best version". You can't fight against the tide.
If you are never going to engage with newer players of the game, then this isn't a problem for you. You have your books and your 17 pages of house rules- Pinkertons aren't going to show up at your house to rip that away from you (we hope)!
However, if you are going to have to engage with newer players, you're kind of in a bind. If they're all playing D&D 5.2024-2025 Pro Edition, and you're not, if you want to play, you have to convert. If you say "I DM a D&D game" and then you reveal "but actually it's D&D 5.2014", you may have to field questions like "why don't you play the new D&D?" and hope you can explain in a logical, concise manner rather than launch into a Grognard tirade that scares them away!
Just like with the 3e/3.5 switchover, WotC will get a lot of people to switch simply by promising a lot of patches. And of course, they'll patch some things but not all the things. And they might create new problems as well. We've already seen in the past 10 years that the design philosophy has changed since 2014, due to new hires, old guard leaving, corporate mandates, and people just changing their minds over time. This will only continue!
If you hated Tasha's Cauldron of Everything, you're probably going to despise D&D 5e 50th (or maybe 51st) anniversary deluxe edition.
I mean, just for myself, I liked 3.5 a lot. Did it have warts? What version of D&D doesn't? When 4e was announced, I assumed it would be a continuation of the design seen in the last few years of 3.5, with Book of Nine Swords, Warlocks, Binders, Totemists and the like being the inspiration. When I saw an actual PHB, I said "yeah, no, this isn't for me.".
Two years later, I was jonesing for a game, and a friend brought me to D&D Encounters. And I was quickly hooked.
So then I liked 4e a lot. Did it have warts? What version of D&D doesn't? WotC made my group dependent on the online content, however, and when that faded from existence, we found we couldn't play the game the same way any longer just using the books we owned. I was forced to switch to other games, and I tried 13th Age and Pathfinder, and even got back into Vampire 20th. I engaged in the Next playtest in good faith, but when the final product came out, it really didn't resemble anything I thought was neat in the playtest.
So I said, nope, not going to do it. But a few years later, once again, I was jonesing for a game and got dragged to the local game store for Adventurer's League. This time I didn't fall in love with 5e, but I acknowledged that I could have fun playing it with the right group and DM.
I don't intend to play Neo 5e Hypercool Kids Edition. But I know that, at some point, I may end up interacting with it in the future. It's inevitable. Even my diehard "AD&D or nothin'!" friend eventually had to sit down at a 5e table, because the amount of people willing to play his edition of choice had dried up.
Because in the end, I love Dungeons & Dragons. It's my favorite game. I may not like the current version, or the company that's in charge of it, but with the right group and the right DM, a lot of sins can be overlooked.
