You can pick whichever contractor you want at any time. It is not necessary that the adjuster and contractor be there together though. Keep in mind that the "contractor" is only a sales person. They like to be there to point out anything and everything to the adjuster. The adjuster doesn't need the contractor to be there to write the claim, but it doesn't hurt to have them there together.
It depends, that is possible. After the last few years of fires, the department of insurance required all insurance companies to make changes to policies that extended certain coverage. Since insurance companies were forced to re-write their policies anyway, they took the time to change some things like material matching and creating roof payment schedules. Basically, the insurance company may no longer have to match a shingle that isn't made anymore, or match siding when the exact color can't be found. Roofers are slow to this info though. Roofers specifically target certain makes and colors of roofs, and go knock on the door and say there is damage, whether there is or not, because in the past if the product couldn't be matched, the insurance policy would pay for an entire new roof. Since the change, roofers have miraculously been able to find materials that "aren't made anymore." Just ask your company about that when you make the claim.
For fences, they usually just pressure wash the fence so it is all fresh wood, and it can age evenly. Unless you have huge dents in the wood, any divots will all work themselves out in probably one season due to moisture and temperature change. You can do absolutely nothing and your fence will likely return to normal by next year, but hail splatter is technically damage, so they'll at least pressure wash it. I assume it's not painted since you said it is cedar. The A/C unit can be combed out and that should be put into the estimate as well.
Finally, more than likely your insurance company will have this storm as a CAT (catastrophe), and a CAT adjuster will show up to do the claim. That makes no difference to you, but you may hear the term "CAT" thrown around. Post up any questions you have.






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