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@hubert-lo
Your theory is correct. I was working on my 500 pearls set when the school update came out. Instead of going for that set I went for the 2 new lower sets (100 pearls + 20 pearls) to get 2 upgrade off the sling shot before continuing with the old path.
If I would have horded black pearls for a while I probably have enough to get all Pirate hats first. Then work backward.
IMO Rovio should not release lower level hats, everything need to go forward only.