I saw orgmode once and I really loved it. Used Doomed and spacemacs. But dear Lord, does everything break on updates and need fixing. I had to give up as I just don't think it's feasible for me to fix my emacs when I want to get some work done.
But I agree that it is very stable and for me also doesn't break, even though I use use-package a lot and install many key packages. Maybe it is important to note, that I don't need everything there is out there and that I remove not well working packages quickly after trying them. From time to time I also look at my init file and get rid of no longer used stuff.
I've been using emacs every day all day every time I'm front of a computer, since 1991. I need only one finger to count the pieces of software I've been using that long that have never crashed or broken on me in any way.
I have also run into compatibility issues when using older versions of Emacs with newer packages, and newer Emacs versions with older packages.
[1]: I totally did not build my blog on top of a bunch of these quirks. Every time one of them is fixed I'm reminded of the workflow xkcd. https://m.xkcd.com/1172/
Emacs is a kitchen and emacs-packages are recipes - they come with the exact instructions (source code). If you try to cook fifty different meals all at once, your kitchen inevitably would be a mess. You need to know what you're trying to cook and how to work the recipes, and that comes with experience. No starter kit gives you a structure to un-mess your kitchen magically. Every sufficiently complex Emacs config is a system - a composite interweaving network of thousands of expressions, millions of code lines - it is the Space Shuttle equivalent; Neovim is like a simple twin-engine and VSCode is like a Cessna in comparison. Updates break your Emacs, I update things multiple times a week and rarely anything breaks (I consume over 350 packages); when things stop working - it doesn't usually take even a minute to figure out what's up. Yes, it does happen, but not as often as you painted it. On the other hand - when I need to get something done, there's no other tool in existence that can help me better.
I think most of that was because I didn’t understand emacs itself very well, and doom or whatever is an entire extra layer of code and idioms on top of that. Start adding in any custom packages you’ve installed and things get well outside of the realm where a beginner can comprehend them.
Like you, I also now have a pretty large number of packages, and rarely run into issues on update, with any issues that do occur being easy enough to fix. However, I think a lot of that comes from at this point having built my own emacs from the ground up, so I understand what all the components are doing, mostly…
Only once was there a noticeable breakage when a command like `git log` in the terminal would spit out all its output instead of displaying one screenful at a time. I'd expect someone following stable releases wouldn't experience any breakages.