The server client has been this way for a while; it no longer shows your logs/logged actions and dialogue; the only way you'll get it to do that would be by downloading the client from Mojang's Minecraft update blogs or by using an older version of the server client.
Instead, your logs can be found in the generated logs folder- while the server is running, you'll see a 'latest.txt' (or something similar) which will continue to be updated for as long as the server is open. You'll need to look into that file in order to see if there are any problems with your server set up. If there are none (such as keybind failed), you should be good to go.