Our close family friend works for the larger marine underwriter's in Vancouver. Not a broker/agent, but the underwriter and she was just over for a visit so I asked her about this and she said definitely with some boats depending on age, type, use, etc they will ask for a survey and depending on the situation some times an out of water full survey of hull and all parts. The survey is paid by the customer.
For both my boats, every year I keep a detailed updated list of things I've added or done to the boat with a large collection of pictures. I keep all that in a folder marked with the month and year of the updated info and pictures. The more info and detailed notes you have of your boat the better position you will be in with an insurer if something were to happen to warrant a claim.