I recently had a particularly vexing issue in a small encrypted room of 3 people, new messages were shown as undecrytable and then only readable a few hours later, we never figured out why.
I re test it every few months/years because I hear it's getting better, the server is properly configured now, encryption system was remade, there is a new client, etc...
Losing my whole chat history each time made the endeavor even more frustrating. I know not everyone keep logs but I can search my Mails and Irc logs from 20 years ago and I find it really useful.
Sorry for the rant but since you asked. Like I said I fully support your work on Matrix, I just find it so ... frustrating and it make me sad because I really like the idea.
As part of the funding we're setting up a dedicated crypto team (at last) to focus on nothing but the remaining encryption problems. It's super embarassing that these failure modes can still exist today though - sorry :(
To be fair, other E2E chat solutions have similar problems, like Signal. It feels more to me like we did not properly crack this problem yet.
I have yet to try it again but definitely want to.