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@pumpumpum
If you adopt the strategy of saving pearls and buy hats when offered for 5K, I would recommend letting Red, Blues and Chuck go, and concentrate on Terrence and Silver. When a hat event eventually comes up – you need to land on floor 30/35 for those. Matilda will often be offered in the adventure itself, and if you can get 3-4 hats you might get her “for free” then.
You might buy Bomb also, as he is a nice chap on your team. But concentrate on the 2 upper ones.