TL;DR: always update Django to the latest version you can, if your app is a little bit bigger, jump from one LTS to another may take some time. LTS is great, i

TL;DR: always update Django to the latest version you can, if your app is a little bit bigger, jump from one LTS to another may take some time. LTS is great, if there is some reason that you cannot upgrade when new release comes. But if you use any plugins, just update to the latest version your all plugins support. Some plugins like (or even need) to use internal Django API's and if your app becomes pretty big, you may be tempted to use those internals in some places as well, which makes upgrades more painful due to internal API changes. Speaking from personal experience of upgrading pretty big and rather legacy app from Django 1.4 to 1.8. Took more than a week.