There was a thread about how during busy times, steamcmd would time out when doing things like updates and downloads. I think it's a matter of doing the 'yes, update' again and again until it works 'cause my server is started now. Just the busy season with steam sales I guess.
Hello!
I found my new server was unable to start, so I came to the forums. I tried setting the option to 'yes, update' and clicked the green save and restart button. The loading overlay on the page went away. This was about 5 minutes ago, and the server still hasn't started. Not sure if I should just wait longer.