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So it's likely that I'll have 2-5 people accessing the central info.
It's one household so they'll be on the same network but ideally I'd like to be able to sync calendars (and the associated info) at any given time online.
That's where I run out of knowledge, essentially. Setting up a basic CalDAV server (like Baikal for example) isn't beyond the realm of possibility, it's just knowing how to actually get it online.
Would I need my own server in my home, or can I host it similarly to my Wordpress website, for example?
Linode has some cool “turnkey” solutions for this. One example: https://www.linode.com/marketplace/apps/nextcloud/nextcloud/
So instead of doing a reverse proxy or vpn on self hosted hardware you would be renting linode servers that are already connected. Then you just have to follow the instructions to hook up a domain or add the relevant dns records.
Either way is fine it just depends on what you’re comfortable with and what you have on hand/want to buy.