I resurrected a Python project of mine after 7 years. Upgraded the dependency management to Poetry, upgraded the major version of Flask. Boom. Back in business. Try that with a modern Node project after 7 months.
I'm sure there are modern projects that can make this painful, but if you're judicious about dependency management and staying on the LTS version of node, its rare you see any major headaches in our stack.
Even for super old / legacy services (ones without automated dependency mgmt through CI), it takes maybe 15-30m to get everything up to date.
I took a project with ~20 top level dependencies and around 5k lines of Python / Flask (plus a lot of tests). I YOLO'd upgrading everything to their latest versions in 1 shot including Python 2.7 to Python 3.7, Stripe API versions and everything.
I did that around 2.5 years ago and it took around 45 minutes. The app was using SQLAlchemy, Celery and had a bunch of things you'd expect to see in a SAAS app (users, custom admin, payments, custom CLI commands, migrations, etc.).