I asked these same questions to the ABA and this is the response I received:
The reg states that “In connection with the initial purchase of an insurance product or annuity by a consumer from you,….†which seems to indicate that the insurance disclosure need only be provided with the first purchase and not for each subsequent purchase. However, that same language does not appear in the section related to the disclosure provided for insurance sold in connection with credit. That disclosure “must be made orally and in writing at the time the consumer applies for an extension of credit in connection with which an insurance product or annuity is solicited, offered, or sold.†Since there is no language indicating this applies only to the initial extension of credit, it appears to me that the disclosure would need to be made each time. If the consumer applies for a car loan and you want to suggest insurance the loan disclosure is required. If that same consumer applies for a mortgage a few months later and is interested in homeowner’s insurance the disclosure would need to be provided again. That makes sense when you consider that the purpose of the credit disclosure is to remind the consumer that the purchase of insurance though the bank is not a requirement for getting the loan. The purpose of the referral disclosure is just to remind the consumer that the product is not FDIC insured. I think the assumption is that once you have informed the consumer about the FDIC nature of the insurance, you need not inform him again, but the loan disclosure is a different matter.