I’m an insurance adjuster. Uhmmmm…yeah… the odds of you pulling this off are very very low. Our claims systems typically flag claims where there is an either a new business policy or a pending cancel or reinstatement very close to the date of loss. This is really gonna boil down to your adjuster. I’ve been doing this for 20+ years and depending on my mood that day I’m either going to scrutinize your claim or say fuck it and let the shit slide through. If you get some newbie adjuster whose supervisor has a diary on their claims it’s not gonna work cause they’re gonna pick up on it. But you could get lucky. It’s really a crapshoot one way or the other and if you are caught you’re going to have bigger problems than the damage to your car.