Tawawa

Probably, there are references to expeditions everywhere.

This is exactly what guided me when making my choices. (no)

Regarding individual points, there are actually guesses based on knowledge of the interests/tastes/characters of some participants. I can't say that there are many such points, though. In this regard, I find the list of paintings particularly problematic – most of them were probably guided, to a greater or lesser extent, by the principle that Aretz described in the post above. At the very least, this would not be surprising, as I doubt that there are so many connoisseurs/fans of classical painting among Heroes fans, and the chances are high that the choice will fall on something very well-known. In fact, this is what happened with Bosch, mentioned earlier.