Contrary to what some painters may believe insurance protects both you and the Owner. When a painting contractor says they have not seen a sales benefit of insurance it is simply that they are not trained on how to educate the Owner about that benefit. Remember that the Owner is not born with a painting manual in their brain so they do not automatically think in terms of insurance. You need to educate them. The importance of insurance is obvious to the informed purchasers of paint.
Insurance can be a huge benefit if properly positioned.
With your history with this customer it could have become a very significant benefit if you knew how to educate the value of insurance. If he was equally insured then you didn't have an insurance edge. That behavior is very common and is expected by the professional and that is why we have specific WordTracks we use during the Measure Call that educates the Owner and helps them avoid making the same mistake. Selling is education following a specific process. The process is built on a foundation.