> Given that it comes with issues, I assume the benefits outweigh the downsides.

Any change can introduce regressions or break habits. The move toward socket activation for sshd is part of a larger change in Debian. I don't think the Debian maintainers changed that just for the fun of it. I can think of two benefits:

+ A service can restart without interruption, since the socket will buffer the requests during the restart.

+ Dependencies are simpler and faster (waiting for a service to start and accept requests is costly).

My experience is that these points largely outweigh the downsides (the only one I can think of is that the socket could be written in two places).