Well, my car got damaged while parked again over the weekend. This time it was a lot less severe than last time. However, it still left enough of a mark to really annoy me. It looks like a parking incident where the car behind me just didn't know how long their car is and hit my rear driver side corner while trying to get out.
Originally I thought maybe I can get away with buffing it out and using some touch-up paint for the damage. Upon closer inspection, the clearcoat is actually cracked. That means the bumper must be repainted.
I made a claim with my insurance company right away, but will see if it is possible to get it painted below the cost of my deductible. See if the shop will cut me a deal if I can remove and reinstall the bumper myself (easy on the Fit, see my Taillight install post on how).