I think he's including the time to learn what he's doing. If you have no clue then it is going to take more than a few hours to learn everything. Sure, once you're competent and everything is set up, it won't take much time. It is just getting to that point that could take a lot of time.
True, but it is more a matter of where you choose to invest your time. Hosting and sysadmin work have nothing to do with my startup's value add, and I personally can't add much value by doing it myself.
Run uPgades, monitor servers, especially free sPace etc. when u upgrade stuff breaks sometimes, write installation scripts, fix them when new version of something comes out. Etc etc etc. we run about a dozen different projects in multiple configurations and since the move to Heroku I'd say we saved amour 20 monthly hours.
That's a lot of time.
What is the most time consuming task when managing your own dedicated server? I thought that it takes max 1h monthly to run "apt-get upgrade".