Heh. Well, ship design aside for now, the Jolly Roger is usually associated strongly with the captain, right? So somehow, it should resemble Lenwood or be somehow representative of Lenwood. So perhaps the skull and crossbones, but with Lenwood's hairstyle would probably be a good starting point at least. His appearance on his profile is awfully lacking. Does he have anything special about his usual outfit that would look good on the JR? Like chains or ropes or...anything?

As for a crew name, there are a few options that I can think of. The first step would be coming up with a nickname for Lenwood to go by. Akin to "Straw-hat" Luffy of the Straw-Hat Pirates or "Whitebeard" of the Whitebeard Pirates. Then you can name the crew after that nickname.

Alternatively, you could give a name that relates to the crew's origins. Since the crew was gathered all at once, and in such a bizarre manner, and each person is so distinct or simply out of the ordinary, you could go with something like the "Misfit Pirates."

Finally, there's always the simple "Lenwood Pirates." It's rather unimaginative, but it's one to fall back on at least. xD

As for the ship...well, honestly, I feel like the ship we start with should be basic and rather dull. The crew can acquire a new ship more tailored to them later somehow like the Straw-Hats got the Merry-Go. Perhaps with our shipwright having helped build it or something.