I've been using Django since v1.0, and when each major version is released, I run through the release notes to see what I need to change. Russell is correct that most things will work from one version to the next, but I like to keep as up to date as possible to minimize my risk of hitting a deprecated feature. Once I build a checklist, I can go through it for each app I support. Doesn't take too long, and I feel I gain a better understanding of the new features this way.
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