OpenSSH right? What version?
No issues with Dropbear

https://blissos.org/

Tested remotely on termux and looks good on small screen

Khal is a nice tui calendar, maybe not for your needs like calendar.txt

What’s wrong with kitty?

I’ve been using kitty for some time didn’t had any issues, and multiplexing is useful.

PS: i used tmux for many years, and still use on headless

Without the soundtrack is just another skate game, THPS had the best soundtracks

Using it for some months

I tried to keep things simple, however I use Kodi mainly with PlexMod addon.

Plex official apps have many issues with audio and subtitles, Kodi plays (almost) everything and better options for audio/subtitles

Kodi: A standalone multimedia player, it plays contents stored locally or on the network (SMB, NFS)

Plex/Jellyfin: Multimedia server, it shares local content over network/internet to multiple users.

Stremio: Plays content from online sources (torrent, HTTP)

Debian can also be FreeBSD https://wiki.debian.org/Debian_GNU/kFreeBSD

Unfortunately died last year