Re: Insurance - who do you have and like?
Switched from Boat US to Progressive and saved a ton of dough on the policy. Progressive is a lot easier to negotiate agreed hull value with, Boat US was a pita. Progressive doesn't seem to offer some of the specialty coverages like freeze damage whereas Boat US does, however Boat US's disclaimer for freeze damage pretty much leaves you SOL in any realistic circumstance ie: negligence cannot be proven on winterization procedure.
I haven't had to make a claim so I can't comment on that subject but I've read Boat US is much better for settling claims like running gear/outdrives damage, stolen gear etc. My main concerns are total loss due to a catastrophic event, or a fuel spill on the river. Both of these scenarios seem to be pretty iron clad with Progressive as it's more along the lines of basic coverage.
So, I would say if you're trying to insure a boat with a lot of gear that could be stolen, or canvas that could be damaged in a wind storm then Boat US would be my choice. But if you're just looking for basic coverage then I'd go with Progressive.
Just my opinion.