Think you're taking him to literally.
I would prefer wonky and authentic than reinagined which usually means watered down, bland,inferior.
This applies to anything old. Eberron yes, Kobra Kai yes, latest Bond movies yes.
New Spelljammer, various reboots and hack jobs no.
You can have quality plus faithful adaption.
If they change what attracted you to the property in the first place it's understandable.
Badly done you don't appeal to the new crowd or the old one.
You've imho misidentified the problem by talking about "wonky and authentic". There's no way you can describe Eberron or modern James Bond movies that way. Cobra Kai sort of is, but more to the point, it's winking and meta, but it comes from a place of real understanding, but also of growing up with something, rather than seeing yourself as the author of something.
Spelljammer is a total mess not because it's not "wonky and authentic". It actually kind of is those things. Spelljammer is a mess because it wasn't understood enough, and the adaption is superficial and lacking in skill. It's not really updated in the way Cobra Kai (the most relevant comparator from your list) is. It doesn't do the clever winking at the audience that CK does. It gets that stuff is ludicrous, but it doesn't know how to acknowledge that and move on, and just has messy stuff that doesn't really work like the Clown Pirates, which something like Cobra Kai would have recognised is almost breaking kayfabe, and too far.
Planescape will probably be a trashfire for similar but worse reasons. I've never seen any evidence at all that anyone at WotC really understood or even loved Planescape, and truly "got it". I'm not saying that idly, but because it's relevant here. You can't modernise Planescape in a way that makes it work like Cobra Kai works, without loving Planescape and getting Planescape. Everything we've seen from WotC over 20+ years now suggests they don't even like Planescape, let alone get it. They've consistently minimized it, or cut it out, and the one time they went into detail, it was
absolute worst possible version of Planescape. That version of Planescape was like Cobra Kai with all the karate removed. Just Daniel-san selling cars, and Johnny Lawrence getting involved in petty crimes and losing low-end jobs.
Faithfulness isn't the key issue, as your examples actually show (modern Bond isn't very "faithful" to older Bond beyond some broad tropes, and some of its attempts to be "faithful" have been dire - SPECTRE for example). The real issues:
A) Skill in adapting/updating something. I honestly don't think WotC has the talent. I don't think WotC has particularly good people in charge. If they bring in some new people, especially from outside of D&D, maybe, but right now? People like Chris Perkins? Nice guy, but not up to the job. Sorry he obviously isn't. You can't have someone like that in charge if you want Cobra Kai.
B) Genuine understanding of the original. I really don't think WotC's leadership particularly understands older D&D settings except maybe Greyhawk and the Forgotten Realms and just possibly Dark Sun (but I'm very unsure about that). I certainly don't think anyone in WotC's D&D management team really understood Spelljammer. I think they quite liked it in a fannish way, but they didn't really get it beyond the superficial. Maybe this is kind of the same as A. You don't really need to love something, here, I'd say, you just need to profoundly "get" it, and I don't think WotC do (loving something can help, but being too much of a fan can also blind you to issues).
C) Enough separation that you don't think of yourself as one of the owners/creators of a thing. Cobra Kai's entire leadership is my age (44-45). They grew up with Karate Kid, but they know they didn't create Karate Kid. WotC has an issue where a lot of the people involved with D&D have been involved with D&D since the '80s or '90s. Perkins since '88 for example - I wasn't even playing D&D then, and that's well over 30 years ago! That's a problem. That's a real problem. It's not his age, to be clear - it's that he's been there the whole time so has a very different understanding of settings to someone who met them as a player/DM.
I think if WotC want to do a truly great updating, they need new people working on it, people who grew up with that setting, and really profoundly get that setting. More likely we'll either get WotC veterans with a proprietorial attitude that blinds them to what actually made the setting great, and what could update well, or some innocent kids in their 20s who just got set on the task, and don't really "get" the setting. Or god help us we'll get Monte Cook.