Or waste his money. I am familiar with the details surrounding the event and it was a very minor charge decades ago, and he wasn't even convicted. Several people both in this thread and via PM have confirmed that they got their licenses despite very similar circumstances and they simply listed the violation on their app on the appropriate space. I highly doubt that the attorneys that cover this sort of thing "most likely have a relationship with the COP" of a town picked out of a hat.
We live in the great USA and it is everyone's right to be able to spend their money as they see fit; if someone feels like they cannot do the research on this or they cannot understand it, people like lawyers and insurance companies will be happy to take your money. As for this I will recommend to him that he just lists it on his application like the several members on here did and I will post the results in the Guide to Gun Rights in your MA Town thread.