They already do. Federal government regularly fails spectacularly and it regularly costs us taxpayers billions. And so do local, state, municipal, etc. governments. Presenting it as if this is some unheard of failure that disqualifies everybody involved including the candidate is silly. A lot of successful websites failed, many multiple times and for prolonged period, despite employing top talent and spending millions on them. Failure is always an option.
His use of "mistakes" is a verbal fallacy called equivocation. Not all mistakes are the same.
wikipedia: Equivocation ("to call by the same name") is classified as both a formal and informal logical fallacy. It is the misleading use of a term with more than one meaning or sense
If you're the prez and express a significant reaction to common scanner technology that's 12 years old, that's news, whether it's "amazed" or "curious".