do any of you hate how self-hosting services like photo- or document-management systems, or even a simple rss tool, forces you to sort your stuff out, and put your decades old files in order?!

What is this "sort" thing you speak of? I don't sort anything, I have NextCloud syncing my entire photos, videos and documents folders and they are just as messy as ever. Granted, I do go through my photos and videos once a year and dump them in a folder named for the year they were taken. Occasionally, I'll go hog wild and try to sort some of a year's photos/videos into folders named after events. Though, that hasn't happened in a number of years. I setup NextCloud so I could have everything synced to my own server and just forget, not have to deal with labeling my data.

As for bookmarks. I already keep those in folders; but, I don't sync those. I use my desktop far more than I use my phone for web browsing. And the types of things I use my phone for (mostly recipes), I just keep bookmarked there.