My experience has been good, with a Django app maintained for over 8 years now. We've only updated Django when a new LTS version is out. That means once ever

My experience has been good, with a Django app maintained for over 8 years now. We've only updated Django when a new LTS version is out. That means once every two years there's an update that may break something, but I don't remember it ever being more than a few hours of work. We do take some care to (mostly) only use documented interfaces, so maybe that helps?