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I dont know about the HP situation. But I know that I have 3 pirates with all pistol pouch upgrades.
Each and every one of them is limited to 175.
I believe when they first added the pouchs there was a bug, that "added" each pouch's additional storage to the total instead of changing it to the new total. Hence one of your pirates may have gotten an additional 25, when upgradeing from the first pouch, to the second pouch.. and its since been fixed in the game (i think).
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