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You should sell when things are hot, people are likely to impulse spend when there's a hot market. Waiting for the value to go up is fine, but if you wait too long the market for it may crash and you lose a large base of your buyer pool. Maybe some simp will be willing to spend big money on that in the future, but it's a gamble since the likelihood of finding a buyer goes down over time. Also there's a chance of a superior version coming out that will make yours undesirable, making the value lessen.
Pic related, when Dark Knight fever was everywhere I sold one of these figures to a guy for $150 in the period when they were pulled from shelves momentarily, I wouldn't even be able to get $3 for it today.
