Very low risk for me. 1 - 5 days max duration. I have a few stocks I do it with. I actually do better quicker when the price drops.
So get the profits from the option trade and the OBC. It's a nice hobby.
I dont dress up. I'm on vacation and it's my preference. Others to dress up. You do what you want.
But...I will often compliment folks who are dressed to the nines. They look great and are having a great time.
I was in Portland as a hotel guest/tourist. On cruise ship day, it was hell for non ship tourists. Nothing available, restaurants packed, no transportation. Next day, back to normal.
Haven't been to Bar Harbor, but these little towns aren't year round stops and they just don't have the infrastructure for massive ships.