I've run into this on a bunch of systems, and it absolutely is a mess. Particularly since Explorer gives all kinds of special status and UI elements to 'Documents' folders - if they just had the same name in different places I'd care way less.
But the solution to "we screwed up years ago" is definitely not "nuke one instance with no warning and don't even glance at what's there".
It's basically the only reason I didn't lose a bunch of data from this bug as an Insider - the "Libraries" and special "My Documents" folders are so damn messy and have caused me data loss at other times, that I stopped using it and manage things myself.
Another lovely one, for ages (probably still) OneDrive would purge it's local copy whenever you turned it off or uninstalled it. That was probably one of the most frustrating things that Windows has ever done to me.
Edit: Lord, can we please talk about "3D Objects" too? Who the hell got promoted for shoving that down everyone's throat in half a dozen places? Every week I get an update I have to run a regedit script to remove all the bullshit they've shoved into Explorer for absolutely no reason.
`Libraries` and `My Documents` an absolute mess, agreed. I've given up and just work from a personal folder that serves the exact same role but doesn't have any special Windows status, which is a pretty serious indictment of those "helpful" features.
A sincere question: why are you an Insider? After the Windows 8.1 issues I'd be really gunshy about getting early anything for Windows. Are there upsides to that, or is it pretty much just a public service in the same sense as running nightly Firefox builds?
I like being on the bleeding edge. My only Windows PC is a gaming machine, so I don't mind it updating frequently and/or needing babysitting (for example, the very latest flight added a HyperV adapter and broke my internet, despite having HyperV disabled).
That, and honestly, they're pretty rock-solid. Other than this net adapter this thing past week, I've never had anything truly disruptive. OTOH, there've been a time or two that I was glad to be an insider because of a bugfix or feature that wasn't likely to be backported to stable.
And some misplaced desire to help? I can rationalize it with OSS, I can't really tell you why I feel some sort of responsibility to do it for Windows too.
That makes sense actually, thanks. I don't think Microsoft is inherently evil or anything, nothing wrong with trying to help make software better even when it's not OSS.
My confusion was mostly just that I couldn't picture who would have the tech background and Windows familiarity to fix (and productively evaluate) weird or buggy releases, but was also willing to have their system destabilized without much warning. For myself, I expect I'd find being an Insider exhausting; even if I know enough to fix the issues, I don't use Windows very often and I'd feel lost whenever things changed and needed to be fixed.
Getting early OS updates sounded much higher-risk than nightly Firefox builds or something. But "it's a gaming machine" actually makes total sense - I forgot how many people have a nice Windows machine they use often, with no real need for it to be stable.
But the solution to "we screwed up years ago" is definitely not "nuke one instance with no warning and don't even glance at what's there".