1-2 times a year when I go to update our app's Webpack, in a matter of 3-4 days I:
1. Get up to date on all recent developments in the world of javascript, babel, esbuild, typescript, eslint, webpack, jest and all their plugins
2. Get the chance to browse through hundreds of fresh github issues while they are still open!
3. Open a few new pull requests
4. Find out about tens of of plugins that are not being developed anymore and their new replacements which are almost the same only with a new name and slightly different API!
5. Give my laptop and build server's CPU's a good go
6. Call my therapist
It's a wonderful opportunity to keep life on edge.
The release was rushed by community pressure, and now we have a half-baked upgrade strategy. I would've happily waited another 6-12 months before v5 was released to get major plugins ready first.
Don't try converting a large legacy-ish codebase :)
I do want to try snowpack too though.
Mind you that's not necessarily a direct result of the tools or those using the tools. On the other hand, resources are finite. Any time used for X (e.g., wresting with Webpack) "comes out of the budget" for Y (e.g., bug fixes) or Z (e.g., a UX designer).
Clients/customers care about their users/end-customers. And users/end-customers don't give a toss about Webpack or anything else. They care about themselves. Full stop.
This is just in the nature of progress. If any product owner was fine with a simple static website which only displays some text, I'm sure there wouldn't be any noticeable bugs in it.