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Look up C.L.U.E. report. Too many claims could have your premiums raised and if you shop insurance other companies will know and you may run into sticker shock.
Also just remember what you say or ask an agent could be used against you. Agents do take notes for their own protection.
My wife nailed three of the four corners on the newer (then) pickup over time - not bad, but two were very noticeable (rear was really just plastic trim). Parking stuff - single vehicle vs. a boulder, post, etc). My deductible is $500. Three fixes would have been 1500 out of pocket. Recently I had the damage fixed and it was 1600 bucks for everything. Looks like new. So making multiple insurance claims at fault would have raised rates and at the end of the day not really contributed to the repair costs. YMMV.