I would say either tell him the whole amount is due right away or the insurance claim gets filed. Otherwise if he decides to stop paying you'll only have small claims court to fall back on.
but if he doesn't pay me when he promised, i can just file the claim with my insurance and not have to worry about it at all. so i'm giving him a chance to pay me, then if he doesn't i just go through insurance like i would have in the first place.
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