Summary: the problem with Pascal's Mugging arguments is that, intuitively, some probabilities are just too small to care about. There might be a principled reason for ignoring some probabilities, namely that they violate an implicit assumption behind expected utility theory. This suggests a possible approach for formally defining a "probability small enough to ignore", though there's still a bit of arbitrariness in it.
Sure. But there is still some internal, objective measure of value of experiences. The constraints you add make it harder to determine what they are. But in simple cases, like trading ice cream, it's easy to determine how much value a person has for a thing.