It's a fascinating comment, in a few ways. I can say I have never been somewhere and wondered 'would a Google streetmap car come here', I don't think it works in that way. The closest similar judgement I can relate to is being somewhere without network coverage. I don't really want to be there, it's weird and makes me think about how different it would be to live somewhere with no coverage. So perhaps then, it's simply noticing the absence of something we thought if as ubiquitous. A mental model, revealed as wrong, or distorted.
Jarring is a good term for that too.
It looks like it would have taken the driver perhaps 10 minutes to negotiate the town, significantly improving the imagery. I would be interested to know how Google determines what should and shouldn't be included at locations such as these.
I've made a list of similar 'one-horse'-type towns to visit during a future one-in-a-lifetime trip around my home country (Australia). Growing up in a country town there (population roughly 25k at that time), things are indeed different than in the capital cities, and I imagine even 'more different' the smaller the population.
Not trying to be offensive here, I just find the thought of using Google Street View coverage as any kind of metric for such a place so... jarring.