Insurance
Definitely a product you want to shop around for. As an example, I get most of my boat insurance from a broker I have used for 30+ years. Currently I have two boats with them. A 22' Boston Whaler in California and a 31' Devlin (wood) I keep in Washington (in sale process at the moment). Both were underwritten by Ace a large insurer of boats. However Ace did not want my 22' Donzi unless I paid a ridiculous price (performance image??). State Farm (where I have auto and house insurance) gave me a great price on the Donzi and had no performance issues. Of course I have a stock 300hp Donzi so there is really no performance to be concerned with. Haggerty has in my opinion always insured what others don't want (high dollar classic boats) and their prices reflect that.
I also tend to go with very high deductibles (self insure on the small stuff) which keeps the premium down.
1967 Triple Hatch 18' (sold)
1969 Holman&Moody 18 2+3
1982 454 TRS no windshield 22 2+3 (sold I'm an idiot)
1997 454/Bravo 1 22 2+3
+ some less cool, more functional boats