Shipping claims are very difficult, but if it's legit, not a big deal. I just had both a USPS and Fed Ex claim approved without any hassle at all. However, I needed to provide pictures of the damage and proof of value. Proof of value is the hard one. If you just want to use what you paid/charged for it, not too hard, you can just provide the email of the transaction. But if you gave something to someone, then it starts to get hard quickly. You have to find a closed ebay auction of the same (or very similar item), or public posting (here or on RGVAC) of people advertising the item.
Major important point: Proof of value overrides amount insured EVERY SINGLE TIME (up to the amount insured).
If you insure a Pac Man marquee for $100, you ain't going to get that, unless you can prove it's worth that. And you aren't going to be able to do that. So over-insuring something, "just in case" is money wasted, totally just thrown away. And if you insure a tested working Quantum PCB for just the default $100, that's all you are going to get, even if you can provide 25 references of proof that it's worth a lot more.