It took me 30 minutes restarting the "Initialization" so it can fully download the mods. Do I have to do this (download mods for the server) everytime I launch the server?
#Do I have to "initialize" my co-op server everytime?
fossil river
iron crag
This is largely down to how Steam workshop feels about letting your server download/update the mods it uses, unfortunately. I'd assume fewer mods mean fewer opportunities for the downloader to just decide it doesn't want to work anymore?