Okay, this is where you go, you start from the beginning, well one of the beginnings, you either start with the cutie mark story or you reveal that through flashbacks and start with the Hippie going on his journey to find his friends.
He's sounds rich and a bit naive so I say you start of that story with him finding out about some sort of rumor or map or information about this missing adventurer.
He sees this as an excellent useo f his time but knows he needs friends, a crew, and he hears about the closest one through some m means, he he goes on a breif short range journey to convince this friend of this plan. I'm not sure how, maybe thsi friend is in jail, or some other dangerous situation, it something that'll shwocase both of their abilities in intellect and combat.
Next this lad will return home, he is of higher class, yes? Well then while he is defiant of this backing, I'm sure his much smarter fiend will be able to let him know they can take advantage of this to get supplies like say ship or something. At first the fmaily should adamantly opposed to it, so our heroes will "borrow" the bits in the middle of the night, and take flight, becoming outlaws in their own home while they follow this lead.
at their first stop, they should be looking for rumors on two things "Information on their adventurer" and "Information on one of their old friends". One may lead into another, but I think it oculd be spun into a kidnapping story involving one of the rival pirate gangs also looking for this adventurer.
Our heroes help retrieve their friend and get their information and move on, you try the three-colt dynamic for a bit, maybe while they go to one of the rumored last locations of the Adventurer, maybe a lost island or a tomb where they have to go through Indiana Jones-like escapades only to find a piece of map or some clue that shows the adventurer was there, left his mark, and has moved on to bigger and better things.
You sort of repeat the patterns little bit with a bit more intrigue, like they find themselves in a land where they're unwanted, one of their friends is against them at first, they encounter another rival pirate crew, perhaps trouble with the law, I'm thinking several false leads and the mean characters getting tricked occasionally by cons trying to separate the fools from their money in exchange for fake information.
All the while developing the crew and their various traits and quirks in the wide variety of scenarios while following the elusive trial of this adventurer and each clue they find seems to be part of some larger whole, who knows, maybe a grand treasure, maybe a superweapon, maybe a lost world, maybe a new alcorn, it's up to you.
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