Welcome to you and Captain Jack! We have a great many fans of Johnny Depp and the Pirate genre! I went through my own grooming attempts but usually defer to the professionals. Ben will behave much better for those he does not know when it comes to grooming. He knows he can get by with too much with me.
But I do trim in between so I can stretch the professional grooming out a little longer than normal. Best advice I got on here was to buy a little Wahl Peanut trimmer -- it s advertised as the little trimmer with big clipper power, and that is true. It really makes trimming the hair between the pads, sanitary area, and ears easier. I liked mine so much that when they came out with a cordless version, I bought that too.