A decade ago, I was very involved in
@Kleros_io, and what I called then "subjective oracles" (opposed to deterministic oracle a la Chainlink) is incredibly hard to implement in a decentralized way because game theory will always favor nitpicking and trying to rob users, especially in "nothing at stake" situations.
Long term, this erodes trust in the system and drives users away.
Kleros solution was to impose a stake from the jurors and allow ever-increasing staked "challenges" to make game theory work for the benefit of users, wasn't perfect, was slow, was costly but quite efficient.
Another solution is centralisation, but that prevents deflecting liability, and my guess is
@Polymarket really wants to avoid that.
Anyway, now that Polymarket has been wearing the big boi pants for a while, their current biggest challenge is improving this resolution system, because things like MSTR will happen more and more often, and the stakes are getting increasingly large.