Just to get this out of the way, 5e is my favorite edition of D&D (playing since Moldvay Red Box Basic), and I like the most recent OneD&D changes. So rules-wise I'm there. Even if D&D 5e isn't my favorite D&D-like game. (That's 13th Age, and a 2nd edition of that is in the works.)
The biggest issues that would make me drop 50th Anniversary D&D are:
1. My group not changing. It's several groups, but with overlap. I run 5e because the group like it, but I have lots of other RPGs I'd love a chance to run. If the other DM in the extended group stays with 2014!5e, I won't even bother to pick up the core rules. And he's been making noises about switching to yet a different system, like PF2revised or the new MCDM RPG, so we'll see what the future bring.
2. It becoming subscription. While I don't use DnDBeyond, I don't mind the increase in price and bundled with that material - seeing how little many in the industry get paid I'm all for the 800lb gorilla in the room to charge more for books so they can raise their prices as well. But with 4e between the publishing schedule and the constant errata I just went subscription, and when they ditched it (which WotC has a repeated history of doing) I had not enough left to play how I wanted to. Wizards gave me what they said with their subscription, but I still feel burned by when they pulled the plug as opposed to me pulling the plug and will not do that again.
3. Wizards again showing they are a poor steward of D&D. The OGL debacle had me swearing off any new purchases, and that was barely reversed by someoen stepping up, and the release of the 5e SRD into CC. However, WotC never has agreed that they can't change the OGL, nor have they followed through to put the 3ed and 3.5 SRDs into CC like Kyle said they were going to do by the end of 2023. A lot of older d20 games, including 13th Age that I mentioned above, rely on those for sales of existing books. Them not following through with their CC promise once the furor died down shows me that they haven't actually learned, just made whatever consessions were demanded to back off the bad press. So I'm hair-edge of swearing off WotC purchasing if they again show they are mistreating the brand.