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If Dreadwing is equipped with Combat Training and 2 weapons and/or armors, does Combat Training give Dreadwing bold/tough 2 since he has 2 weapons/armors? Same question can be asked for Predaking; Does he get Bold 5 if he has 5 weapons and combat training?

No. A single Combat Training gives Bold/Tough 1 at most.
Source: Wizards of the Coast (2019-02-18)    【Link to Ruling】
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