[leetrout]

In very broad terms it's not bad. The docs are great and they give specific advice for upgrades.

With that said you may find many 3rd party apps / utils lagging. A couple libs I use still don't support new style middleware, for instance.

With 2.0 dropping support for py2.7 this might cause more pain points for poorly maintained libs but all in all keeping up with Django releases is pretty straightforward and almost always worth it.

Source: happily using Django since 2008.