Instead of feeling like you are gambling on a potential upgrade my perception is now I'd be gambling on a potential loss / failure-to-deliver if I bought a used car from Tesla. It's only one datapoint, but it's the only data point I have.
Were it the case, we'd have never heard anything from this customer. Happy customers rarely make the news.
There are all sorts of stories of "company I love screwed up and really came through!" Hell, apple gets all sorts of these comments when they do some out of apple care thing.
But yes, it's extremely weird that they didn't just immediately apologize and offer him a nice discount on a different car.
How do they not have a dedicated test fleet?
...then I got to the part where (allegedly), Elon Musk literally took his car, never delivered it, and pretty much just fucked Kevin over super bad.
Elon seems like a pretty smart guy, he must realize he is quite famous, so if there is any way this can be corroborated, it will play negatively all over techcrunch for the next few days.
edit: I accidentally implied fact checking and corroboration are important factors to Techcrunch when publishing.