I removed the name of the vendor--lest this be just what we call a "vendor rant." We don't let people go off on vendor rants--but we all rant on things in general
Your experience is good information for anyone looking for insurance from any company anywhere. We all have to be sure we're comparing apples-to-apples on the insurance quotes. Often we're not and then we get a rude awakening when the "real" quote comes in once all the facts are revealed both ways to the insurer and to the boat owner.
I figure that the 5 other quotes you got were perhaps even near priced to the $2700 quote but the allure of the $1000 insurance was enough to get you to go ahead with a survey. Regarding that survey--if you'd previously had your prior surveyor stop by and verify that the work was done previously (would have likely cost you about that same $150) then you'd probably not have had the local surveyor do the verification. Post survey, many insurance companies will accept a statement from the boat owner on "certain" things but not on others--so depending on what needed checking and the actual insurer, you'd have been stuck with it no matter the insurer.
The choice of five different insurers is alot--figure it was five different brokers rather than actual insurers (underwriters)? Often you'll talk with a broker who doesn't have all the facts right (like that a particular insurer he/she uses isn't going to insure an older boat) because things do change with the actual underwriters all the time. Then, you're disappointed when you get the current scoop on how things are today.
Your situation is a word-to-the-wise for anyone looking for insurance to make sure of what you're being offered in the particular circumstance.
As the owner cruising an "older" wooden boat (81 years old this year!)
I am well aware of the difficulties of finding good insurance at a good price. In our case, we bypassed brokers and went straight to the insurers with a huge document including survey, details of construction, pics of recent rebuild and so forth. In our case, we were ultimately insured by a company that, by policy, doesn't even insure wood boats--nor really old ones--at all--but (as I had hoped) they really liked the quality of work and detailed information we provided to them so they wanted to insure OUR boat.
And that's the thing about insurance--even if an insurer CAN insure your boat, it doesn't mean that they will insure your particular vessel. It's up to them to decide and, unfortunately, that can be frustrating for the owner of an older vessel.
What kind of boat is it? How old? There are special insurance companies which cater to older vessels and older cruising boats, too.
Assume you've insured your boat with one of the other 5 quotes and that you'll be happy with that.