Django is a good py web framework. Sqlite should suffice for such a small app. Once you get a bunch of users and writing action, a rdbms like postgress might be required.

I think some of the kanban style tools out there allow for daily tasks, like asana or trello, wekan. Not sure if those ones specifically do, but it’s a starting point.

I’d say it depends. I run BSD’s in my setup, with a freebsd “development” server running a bunch of jails for projects. I find that easier to maintain than a vm host lately. I just have one more vm to port over to a jail, then I’m retiring my 12 year old server, and looking for a new one.

I have another freebsd box running as a file server for the house, where I drop all our media and a copy of important backups.

I kind of use bsd jails like containers. Once I get one working, I can package it and send it to a server, jnpackage it, and run it with minimal effort/reconfiguration.