What I can't figure out is why you think helping him fuck a Houston escort will shield him from a gold digger in Oceanside, or wherever else he will spend his off duty hours.
I think it would be a regrettable decision. But congratulations on having a stand up grandson. He'll either do fine, or he won't, but either way your involvement at this stage of his development would probably only complicate matters for him.
Thank goodness the current CINC will be relieved in 18 months; that's reason to celebrate imo.