You’re on the right track with the cedar. I searched for cedar shake style siding and came across this product that looks similar. https://www.jameshardie.com/product-catalog/exterior-siding-products/hardie-shingle-siding/straight-edge-panel/statement-collection-colors/

I used to be an insurance adjuster. Coverage for this is questionable and the damages would likely be under your deductible. This is a workmanship issue, so the J channel itself isn’t covered. The (hopefully minimal) ensuing water damage would likely be covered, though. My main concern is water inside the wall saturating insulation and creating a mold issue.

If there was significant water inside the wall, the amount of covered damage could escalate to the point that it would be worth putting in a claim. Just know that coverage isn’t as straightforward as the previous comment made it sound.

I’ve heard that an oil primer is the way to go for kitchen cabinets. Wood filler or bondo should work for repairing those edges.

Those connectors look much nicer than the ones I used, but yes a stretch of wire is the correct way to have a permanently unit section.

Hiding the dollar amounts from the contractor might not be worthwhile unless you were paid for the entire claim upfront. Insurance companies reimburse “recoverable depreciation” based on your actual incurred expenses. This means that any amount you save from the contractor just ends up staying in the insurance company’s pocket. Of course, if you are paid the full amount upfront, this doesn’t apply.

Example: Insurance estimates $20k damage, $5k recoverable depreciation, $1k deductible. You get a check for $14k. If your contractor says they will do the work for $15k, you don’t get any more money from the insurance company and the insurance company gets to keep that $5k.

Note that the insurance company’s estimate is usually fair when it comes to the dollar amount for the scope of work. One minor exception to this is when an estimate is generated very soon after a large storm event. In that case, the insurance company will usually update the estimate to a newer price list if you ask them to.