First of all, all-around antifragility sounds very good in theory, but in real life you'd find that buying every tail to be completely protected is an unrealistic proposition. There are numerous scenarios possible and if you going to spend money and effort to protect yourself against it, you gonna have very little left.
Second of all, most people would zoom-in on some very specific risks and ignore other risks. A buddy of mine was telling me that he's treated a guy who got into a car accident - he was not wearing a seat belt, but at his house he had a bunker with canned food, guns and bugout gear.
Finally, probability of tail events is, by definition, hard to know. So you don't want to be too long and you definitely don't want to be short. However, it's worth owning some modicum of tails to avoid a complete blow-up.