I work with both node and Python. The difference in upgrade experiences is measured in several orders of magnitude. My most recent few projects jumped Python versions because features I wanted were introduced. I cannot remember a time I had to rewrite application code because of an upgraded Python version (well I do, it was the Python 2 to 3 migration a very long time ago).

In the meantime new node versions constantly break backwards compatibility. Upgrading packages is a mess. Runtime environments are not properly isolated, third party packages sometimes explicitly do not work with specific versions of node, etc. For a community so focused on creating tooling, it has the worst tools of any ecosystem I have seen. I would rather work with C than with node.

Oh man 12 -> 20 must have hurt. In my experience, Node really stepped up their game in most any regard after the iojs split, and these days I've had almost zero problems jumping from one major LTS release to the next.

Can't guarantee no issues, but my gut feel is you'll have a much better experience with 20 -> 24 for example.

I know it doesn't always work out, but it definitely helps to keep current, rather than performing a massive update every X years. Most of the time the changes are minimal, but they add up over several major revisions.

Of course, every now and then something like eslint will completely break every project in existence by changing the configuration format, then you have to wait for all of the plugins to be updated (if ever), then hope all your linting rules are still valid... yeah I'm still bitter about that one.

Picking Javascript as the foundation of your project and being dismayed at how much work it takes to keep up is a restatement of the definition of insanity.