He doesn't need to be an IT Specialist to run his own server, an IT specialist will be able to diagnose and fix a number of problems, on different servers, quickly and efficiently. Similar to how a photographer will be able to capture the good moments across different scenarios and be prepared and backed up etc etc,
All he needs is a small server for small traffic, if the server does have downtime, its not a big loss and he doesn't need to be able to diagnose OTHER servers. Hell the only reason you hear big woop about ISP and Network providers fighting downtime is because on any given day their server is down theres hundreds if not thousands of people trying to reach it. For a small time tog, there might be a couple clients a week.
So back to your metaphor, If a photographer misses the kiss during the wedding, OUCH.
If a server goes down for a day, on the unlikely event that your clients were trying to reach it, you bring it back up and let your clients know its back, it may have hurt their estime of you a small bit, but probably not enough to matter unless its a commercial grade client paying you up the ass at which point the whole running your own server is moot.