Excellent questions.
Recently I encountered MTU/MSS issues with (debian) wg clients
connecting to my (FreeBSD, mtu 1420) vpn server. In my situation,
setting the MTU of the debian wg-clients` wg interface to 1392 proved to
be a stable workaround for remote-clients connecting over my pppoe
internet connection. I 've never tried setting the mtu on the FreeBSD
vpn server to anything other than 1420 though because I quickly
suspected my router/pppoe setup to be somehow involved.
I figured my issues might be partly due to the cumulative penalties
vlan/pppoe encapsulation impose on max MTU and might be related to
incorrectly configured mss-clamping in my mpd5 daemon.Not quite sure on
how to further troubleshoot either and because the lowered MTU for
internet-connecting clients is quite effective I quickly dropped the
issue :)