Well, there were a few things in the 2.x series (e.g. naming of default auth views) which ended up breaking existing code and needed updates. But in all honest

Well, there were a few things in the 2.x series (e.g. naming of default auth views) which ended up breaking existing code and needed updates. But in all honesty: django is the project I would worry about the least here. Even when stuff is deprecated, an improved alternative tends to exist and is pretty well documented. The level of care that goes into each release is very high; the number of brown bag bugs that get out very low. If you want a quiet life, django is a very good fit.