I'm eying Matrix, together with Fluffychat. I guess that when reactions will be there (for feature parity between clients, I don't want to miss some important information someone sent as a reaction like "I arrive at 8 tomorrow, can you pick me up at the train station" -> thumbs up) plus a few nitpicks, I'll be able to consider it ready.
What happens next? I am not sure. I would like to onboard them on a different homeserver, but I might tinker a bit too much with my personal server for this, plus it would be unavailable when moving around, etc. So I guess I should set up a cloud-hosted homeserver, but I am afraid of the costs, especially if they start joining busy rooms.
The best answer would be to use decentralized identities[1] on my HS for now, and migrate them over to a backup one in case of an outage, but we're not there yet. That's the main reason I keep an eye on p2p Matrix work with Dendrite (then, because it's more generally awesome).
I do not appear to have the persuasive skills, clout, or sheer dominance over my family members that some of the more Matrix-successful fellow geeks here do :-D