@celesteh @monocles @Steldamm @kkarhan my experience was that hosting an XMPP server lead pretty quickly to having friends and family use it, although there were a couple additional factors:
* family members (who are pretty normal people) got an account on that server, so they only had to install conversations on their phone
* most of our friends are of the FLOSS-nerd variety, and there are enough who are able to run their own server to provide for themselves and for the non-uploading nerds of the group, but everybody had at least some motivation, once the effort required was low
* I'm not on other chat systems (other than IRC, which I'm not going to recommend to family members :) )