@b0rk Semi-answering your other question about Django, itβs reassuring that the framework has been developed for 20 years means the chances of it still running well in another twenty are not bad. The mature tools are better at surviving, I think.
Recently I upgraded a neglected project running version 1.11 (under Python 2) to the newest 5.2 LTS and the site is running happily with it. Interestingly the only problem-maker was a third party plugin.