I could write 10 pages on how insurance works, but I'll try to condense it. Short of it is- Insurance companies are in business to make money- not pay claims. Vintage decks would be a great example. To an insurance company a deck of Bikes made in 1900 would be no different than a deck made to day. One example I use a lot- Say you have a 200 year old Oak table worth $10,000. If you did not have special insurance on the table. The insurance company is going to replace it with one of like quality- You might get a $100 table from Ikea, and this is not an exaggeration.
Keep records of purchases. You may not get full value, but would do better than someone that didn't keep records.
I worked briefly for a health insurance company - Rob speaks the truth, big time. We processed claims for a decent-sized school system's employees. I had to do really terrible stuff because of how the company's policy was written. The one I hated the least was dealing with pregnancy claims.
Imagine you're a female teacher in this system, you get pregnant and go to a hospital to have your baby. Your hospital visit would be covered because you had a medical condition, pregnancy. If your baby was born completely healthy, however, coverage was denied for the baby because it didn't have a condition. Only if your baby was born ill or injured did the child's hospital stay get covered. Such hospital stays for a healthy baby for just two days or so were billed out by the hospital often as high as $2000-$3000, and parents of healthy children had to pay all of that out of pocket. It's almost like a "sin tax" for the dubious sin of being a parent.
Granted, this was over two decades ago, but I can't imagine it's gotten all that much better, especially in those areas of the country where a single insurance company is the only game in town, giving them de facto monopoly control over the region.
Having said all of that, when Rob refers to "special insurance", he's talking about a rider added to a policy. For example, I have a family member who has a noteworthy collection of jewelry - they have a rider added to the homeowner's policy that provides additional coverage for that jewelry, with a slight discount for the fact that most of it resides in a safe that's bolted into the house as opposed to just sitting in a jewelry box on the dresser.
The cool thing about the rider is that you can actually be covered for loss of the possessions when you take them with you. It's really a feature of the homeowner's policy (or apartment renter's, whichever applies). When my car was broken into, my car policy didn't cover loss of possessions in the car - but my homeowner's policy, no rider, did cover me, though they do make you jump through hoops to get the cash.
Riders are interesting. You can add riders for all sorts of things, but it really boils down to the type and amount of coverage you want and are willing to pay for. If you have something that's of special monetary value (the limits of which are likely defined in your insurance policy), you get a rider for it, you document that you possess it and you keep abreast of the market value - if you ever have to make a claim, you'll have everything at your fingertips (except a police report, if the loss was due to theft).
Make especially certain that your policy will cover the likely kinds of loss you might experience. For example, no homeowner's policy issued by an insurance company today covers you for flooding caused by environmental conditions (as opposed to a plumbing accident) - since 1968, only the Federal government sells flood insurance in the US, and I'm told it's not cheap. If you live in an area that's prone to flooding, you should already know all about this and have the insurance for your property.
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