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Your insurance company is only concerned about 2 specific things (and don't take an agent's word on it talk to a claims adjuster): 1) Does the vehicle meet the definition of an "insured vehicle." This means does it qualify for the policy and/or is it the vehicle listed on the policy. If you...

From the discussions I've had with LEOs (including MV owners) a 5 ton requires a Class A license. It can be a CDL or non-CDL but due to the weight you need the upgrade. And it doesn't matter if the truck is registered as a former military vehicle or not, still need the Class A.