re: Jewelry Insurance…. Is it worth it?

Especially when you're dealing with historical shite not of extreme value, eventually you will pay premiums that outweigh the replacement of the item. I've already done that with VPP; spent $3k on a rifle I've owned for so long that I've paid probably $4k in a premiums.

Jewelry is never worth what it is bought or insured for.
To make this easier to grok, OP, take the jewelry you're worried about to a jeweler, and ask them to value it. It will probably be for 25% of what you're trying to insure it for. It was so much fun that we never even asked for my ex-wife's first engagement ring back from the seller, it wasn't worth it.