[Toronto] Two in one claim?

Last week we had a pretty severe windstorm in the greater Toronto area and the shingles off my landlord’s home flew off the roof and landed all over my car which scratched my roof, quarter panel, rear bumper, trunk, and spoiler. Some of those scratches left exposed metal.

Not noticing the damage until I arrived at work and making a call to my insurance, a coworker pulled up and strong winds blew his door into my rear quarter panel that had scratches from shingles falling. Leaving a deep dent and chipped paint.

The next day I spoke with my landlord to try and get his home owners insurance but he was playing the ignorant card saying policies in all of Canada don’t cover natural disaster / acts of God.

Anyway, I fought with him and he reluctantly agreed to give me $650 cash for damages. My coworker told me he’d pay out of pocket for the dent as well.

Later on I got quotes and most reasonable shops wanted $1600-1800 for all the damage. I asked for separate quotes for dent and shingle damage. Luckily for me, the dent and repaint from the door ding requires blending of the door as well as the rest of the panel which happens to have some of the scratches on it.

It was $900 for the ding, and told my coworker 800 and I’d cover the rest. I was originally going to fix both separately and cough up the remaining, or maybe file a comprehensive claim on my own insurance and come out a little on top.

Now my coworker wants to take it through his insurance because his deductible is only $500.

I’m just wondering if his insurance will still repaint the entire quarter panel because there’s still scratches on it from shingles. If not it’ll leave my car with mismatched paint. And is there any chance I can use his claim to fix the rest of my car? It’s a long shot but just wondering