I think it varies. I moved from 37' to 55', and was not interested in any sort of mentor/training. I cited lifelong boating experience, a pilots license, a violation free drivers license, and never having filed a motor vehicle insurance claim. I know the broker presented me with two viable insurance options, and I believe he had at least one more that he didn't think I should consider. There were no policy contingencies (other than a hurricane plan) and there was no undue financial premium. Underwriters are happy to write policies were they believe the insured can properly manage the associated risks.