The MOTD is generated through PAM, so the fact that you have "UsePAM no"
probably affects your results. In the same vein, you have "PrintMotd
no"... Having the combination of the 2 parameters probably prevents the
motd from being displayed in certain cases.

I'd suggest trying
UsePAM yes
Or
PrintMotd yes

and report what happens.

-- 
ssh logins doesn't show the MOTD when connecting with public key authorisation
https://bugs.launchpad.net/bugs/543767
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