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I know Hagerty allows "occasional" drives to work, I even got it in writing once... but that's the "once or twice a month to show off the car to your buddies" kinda drive to work... I don't think you fall under "occasional" at a regular twice a week, per their definition.
Given how you use the car, you are probably better off with a regular insurance that will cut you a break on the lower mileage you need. Agreed value should cover you financially, too...
Classic policies are cheap just because you don't use the car as a regular appliance. Even one or twice a week is definitely not occasional, I'm not passing judgemetn on that, i'm just saying don't bother with the big classic ins. names because even if you squeak through, they most likely they will deny coverage if something happens on your way to work. Not worth the risk.
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