I won’t go for a dashboard or panel, The server would be controlled solely form SSH.
For OTT management (e.g. managing wordpress) I’d use Jetpack and it’s centralized management page to update the Plugins/Themes etc.
I definitely would. If I had to. and if there is a real need for a control panel, why not plesk or virtualmin which offer much more flexibility.
Package upgrades etc. can be automated form within the OS but then, there can be things that potentially break with updates so testing and due diligence is necessary.