You can only boost once, but you can have as many additional dice as you are able to get.
Weapon master rolls an additional dice, Charging boosts the charge attack.
So a Weapon Master that is charging will roll 4 dice for damage. 2 as the base number. 1 because the attack is boosted. And a final 1 because of Weapon Master's additional dice.
In your situation where a charging weapon master has recieved an additional dice for something else you will indeed roll 5 dice for damage.
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