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ok, lots of discussion today, let me summarize my view and why I think this is reasonable.
There are some issues we have with flask, mainly:
flask itself is (by-design) a micro-framework, it only comes with the bare-bones functionality, views, request handling, templating. Everything else comes from either more-or-less well maintained plugins or we have to write it ourselves. Even such crucial things for us like the flask-admin extension are on the "less well maintained side"
Documentation is thus very fragmented and that multiple extensions work well together is not guaranteed and that they can be updated together is similarly not guaranteed
Compared to that, for django:
Is a large framework, that has most of what we need out of the box (forms, templates, database, migrations, admin, roles, access granularity etc)
Documentation is very good and not fragmented over many places
Since it's one package, the parts are maintained together and are updated at the same time
So, for the longer term I think django is the safe choice, also for handing over to new people.
For how we might do this, I think it is best to do a real rewrite from scratch in django, implementing features from basic to more advanced in small, easy to review PRs.
The list would be
basic django project structure
basic user authentication / creation / etc. for admin users
Sending emails for password reset / error logging
The membership registration / membership status and connected functionality
The event system
SEPA
The main points from the README still stand I'd say, use env for configuration, poetry for dependencies, server-side html templating, no separate frontend framework.
This should be the last issue before the switch to django is done.
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