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Short version: Some(?) Raspi 3 stop responding to SSH after the (correct!) password has been entered.
Attaching a keyboard works, so it's just SSH.
Adding the line IPQoS 0x00
to the file /etc/ssh/sshd_config
solves the issue.
I have no idea what IPQoS is, but I do know it solved the issue of not being able to log in remotely at once. (After restarting the ssh daemon or the raspi.)
[edit]Note: this concerns a fresh install of OctoPi!