@Matt_Noyes The biggest challenge with self hosting communications for me, to date, isn't the email, but instead the calendaring. I had a long career with Lotus Notes calendar, and Google Calendar is still missing features but is popular and functional. I do self host IMAP email, and prefer Horde over Roundcube. Advances on calendaring seemed slow, I would like to know if they have improved.
@ntnsndr Thanks for the mayfirst.org link, I see there are U.S. and Mexican parts. The discussion on reorganizing as a coop is interesting. If such a platform was hosted in Canada, I might be interested. In 2016, I moved all of my web self-hosting to Canada, https://www.quora.com/Whats-a-good-Canadian-web-hosting-provider/ . Choosing across organizational governance and avoiding the U.S. Patriot Act on data access is a dilemma, for a Canadian. @Matt_Noyes
@daviding @Matt_Noyes you can solve both relative cleanly with Cloudron (email server and app management) + NextCloud (calendars, contacts, files). Works fine across several devices. Even easier with a $25/year mayfirst.org membership. https://mayfirst.org/en/member-benefits/