@Martin-Musso, that's a cool idea. I did some research and figured out how to play a playlist and send the output to a Chromecast device:
"c:\Program Files (x86)\VideoLAN\VLC\vlc.exe" c:\playlists\playlist.xspf --sout="#chromecast{ip=192.168.86.25}" --demux-filter=demux_chromecast
But, I haven't figured out how to tell it to resume where it left off. This sortof worked, but only for the first thing in the playlist.
I tried this extension with no joy. https://addons.videolan.org/p/1154044/
If you do try it, you'll want to download it from the Files tab and manually drop it in
C:\Users(your user)\AppData\Roaming\vlc\lua\extensions
If you search and install it from within VLC you'll get an old version that's even worse.
Reference:
https://wiki.videolan.org/VLC_command-line_help/
https://forum.videolan.org/viewtopic.php?t=145868