Control

Unbound is pretty easy if you have experience with editing config files.

I use a combination on ProtonMail and Mailgun. I only have a few automated messages going out with mailgun a month so it's essentially free. I also started using mattermost as a notification channel for different things as well. It has the same API as slack, so you can hook it up to pretty much anything you can hook slack up to.

Have you talked to someone at twilio about a high volume discount?

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.