Interestingly, I have a very different experience than you. I simply have a script that sets up the server. I keep updating the script to make it better each time I hit an edge case. At this point, it's pretty bullet-proof. Updates are automatic and so I can leave the server running for months without any intervention.
Due to my love to shiny things, I keep wanting to find an excuse to move to a PaaS but I can never find a sufficient justification.