For insurance, I think you just contact them and let them know what's going on. Ask them what they want from you and how they'd like to be involved. You're not making a claim on your own property (the other side is supposed to just ameliorate it) but they may want to know if there's something that has happened to the property before (ie: kinda like an accident history on a car).
Quotes wise, I'd get a couple of quotes, but I'd also be certain to be specific in what I am asking for with the quotes. I think mentality wise, it's no different than if you are going to get a quote for damage on a car. It's sometimes not just the specific spot that needs work.
Make sure the quote involves restoring the overall fence to what it was like before. It's not your money, it's likely insurance, so make sure it's done right and it's fair for all parties. Don't squeak in stuff that's obviously not necessary (ie: unreasonable upgrade), but don't undercut yourself for stuff that if unaddressed makes your fence lesser than it was before.
Also, make sure that the quotes are more conservative and will be unlikely to change (materials increase, additional work, etc.) and if there's some parts of the quote that may fluctuate more, potentially have those portions split out so that the other side is aware (although if you have several quotes in the same range, they may not really care if there's not enough detail in the break down). Other parties don't care if the quotes are higher. They just hate paying anything above the agreed upon quoted price once they have committed to a specific amount. They'd be happy if it came below though.
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