I have been using Ubuntu Server for development for over 10 years now. Although I am always using LTS distribution, which is supported for 5 years, there will be a time when the server needs an update only because server software needs some refresh (especially LAMP stack). Of course there is an another way – just compile new version, but in my experience this will screw up your installation (believe me – I tried).
Making distribution update on a desktop is relatively easy process – just use “Upgrade Manager” to start the upgrade procedure, sit down, relax and wait until upgrade is finished. Upgrade via SSH is much more complicated – there is no GUI to help you and SSH connection may drop any time leaving you with a server, which is half-working.