I haven't really put a huge amount of thought into this yet, and the last time I did anything approaching coding was on BASIC on Spectrums and Amstrads as a kid. That said, I'm not stupid but there would be a huge learning curve ahead.
Regarding which character to play, I suppose that could vary somewhat as a few characters were quite well developed in the books. The original Treasure Island is written first person as the young boy Jim Hawkins, but his story doesn't really show much potential beyond the end of Treasure Island long after Flint has died etc.
The obvious choices would be John Silver or Joe Flint, depending on whether you like nice or nasty people. John Silver poses a challenge in terms of the actual figure to model, as he's only got one leg and uses a crutch so it's more than just new skins there.
Joe Flint starts life as a child, witnessing his oppressed and abused mother blowing a fuse and knifing his priest of a father to death. The next you hear of him he's in the Royal Navy as an Officer. He's serving under a bad tempered and stubborn old Captain who wont listen to anyone and Flint keeps suggesting they go privateering. His sadistic tendencies are evident in the way he likes to discipline the crew. He aquires a parrot who dislikes his twisted ways and flies away every time Flint starts off on another of his nasty deeds. The Captain has no time for Flint and ends up running the HMS Elizabeth aground approaching an unknown island without taking soundings as per Flint's advice. Unable to warp the ship free, the crew are forced to set up camp on the island. The Captain turns to the bottle whilst Flint plots a mutiny whilst improvising a smaller vessel from the timbers of the Elizabeth. Flint excels in pitching people against one another, and orchestrates a showdown on the beach between his selected future privateering crew and Captain, the Marines, and those loyal to the crown. Flint leaves the island with the new ship "Walrus" and sets of as a pirate.
John Silver is a big, strong but gentle man. He's an excellent sailor with hoards of natural presence who commands the respect of the men. He is an honest merchant sailor. Off the coast of Africa his ship is attacked by pirates and as his Captain and crew are slaughtered around him he kills 3 pirates attacking him before the pirate Captain calls a truce. Seeing John Silver's obvious strength and natural fighting ability (though he'd never killed a man til now) he offers Silver the chance to join the pirate crew instead of being killed. John Silver joins Captain England. England makes Silver an Officer and tries to teach him to navigate, but Silver just can't get his head around the subject. When England dies later on, the crew vote Silver as Captain.
Eventually, Flint and Silver cross paths and agree to join forces. Silver reasons that since he can't navigate for toffee, Flint should be Captain. Silver's crew tacitly agree but remain loyal to Silver.
Flint manages to pick up Selena, a beautiful African slave girl wanted for a murder of the plantation owner she was enslaved to. Selena sails with them, but refuses Flint's advances. Silver had mistaken her for a prostitute in a tavern but although their relationship got off to a cringeable start, she slowly begins to see John's qualities and they get along better, though Silver keeps his distance.
Flint and Silver are good friends, but against Silver's better judgement Flint hangs around too long off one particular island. By now, Flint has become somewhat jealous of Silver's respect from the men, and his plutonic relationship with Selena. Silver's fears are borne out, and one day Flint engages a ship with an armed, ready, but hidden crew. When the Walrus pulls along side to leeward, both ships heeled over in the wind, the "victim" rakes their deck with cannon and musket fire. Half the crew, waiting to board, are wiped out and Silver takes a cannon ball through the thigh severing his leg. The ship's level headed surgeon (whom Selena confides in, and whom Flint eventually murders as he does with everyone who learns enough to be a threat) amputes the leg.
Flint sees this as an opportunity to hijack Silver's respect from the men by mocking him, and Flint's brawny ex-first mate Billy Bones is even happier. He and Silver never got along, and he was intensely jealous of Flint's respect for Silver. Billy Bones makes a comment on deck which makes all the hands laugh at Silver, who challenges Bones to a fight. Silver cracks Bones between the eyes with his crutch, lunges forward and headbutts him knocking him down, then pins him to the deck until he admits defeat. Silver regains the utmost respect from all hands and Bones is put firmly in his place but with a resentment that never goes... Also, during a storm, Silver ends up sleeping with Selena. Flint is livid.
They soon take another ship. Smaller, but good, and Silver suggests that he takes his men to crew the new ship and they sail under Flint's command. Silver and Flint's relationship is tense now, so not sharing the same ship is agreed to be a good thing. Flint wont let Selena leave the Walrus though.
They sail together, Walrus and Lion for some time and amass some fortune. Flint decides that the treasure should be buried on his island from the beginning, so that he can dispose of the crew and come back at a later date and claim every last penny for himself. Silver warns that it's a stupid idea, but eventually the crew (not the brightest lot) fall for Flint's shaky arguement and agree to bury the treasure on the island. Flint takes a crew of six to secret locations to bury the treasure, but kills them afterwards so only he knows where it is. Such is his distrust for Silver now who is clearly on to him, he orders Walrus to fire on Lion should Silver attempt to go ashore or leave on his own. Flint has planted Bones onboard Lion as Silver's prisoner with a sabotage plan.
In the morning, Flint boards Walrus and begins to execute his plan to get rid of Silver and the Lion crew. Walrus is armed with 6 pounders, Lion with 4. Israel Hands however, Silver's gunner, has a nice brass 9 pounder in the hold which neither ship had room to mount and, uncharacteristically, Flint had allowed Hands to take to Lion and had forgotten all about. Hands is able to lay down many hits on Walrus with the 9pdr and Flint's authority under such pressure almost crumbles, but Bones executes the sabotage plan and sets Lion alight. Silver is forced to abandon the Lion while Flint escapes with a battered Walrus. Silver and his men are marooned on the island with 2 boats and the stores they were able to save from Lion.
Silver knows Flint will be back, and he will have no intention of letting any other man leave alive.
Silver would have killed Bones for the sabotage, but Bones can navigate and Silver knows that to escape, he'll need Bones. The men want to kill him, but Silver must protect him.
Flint does return, but with 4 large ships in tow with the Indian "Patang" aboard, who are agreed to be displaced by colonials in America. Flint wishes to use the Patang warriors as his army against Silver who will have dug in and made preparations. Flint also has Danny Bentham and "his" fleet of 2 pirate ships for extra muscle. Danny is a woman masquarading as a man. At the same time, 3 ships from the Royal Navy have followed them to the island and land at the south end of the island where Lion sank. They are merely looking for "pirates" so Silver has to abandon the stronghold there and move north towards Flint. The Patang warriors ambush the RN landing party and more-or-less drive them back. The 2 sloops however head north looking for the pirates.
There are a series of tactical battles on the island between Silver's men and the Patang. Bentham is actually a lesbian and witnesses Flint threatening Selena. Bentham attacks Flint who kills her. Silver and his remaining men make a break for a longboat on the beach but are caught by the Patang. The Patang chief has realised they are merely an instrument of Flint's plan and they will be killed when it suits him. They wish to leave with Silver and return to their women and children in the 4 ships waiting up north beyond the extensive reefs which only Flint knows the safe passage through before Flint gets to them. Silver gets to the Walrus and sees Selena on the beach. Israel Hands coerces the reluctant crew to row back to the beach (and danger) to pick up Selena whom Silver loves. They all get back to Walrus with Flint's men hot on their tails and make a run for it. Silver rakes one of the closing RN Sloops with cannon fire and heavily damages it. The other just fumbles it's intercept and ends up out of position and well downwind.
Vindictive as his is, Flint, who had smallpox as a child, tries to send a smallpox carrying monkey from the island aboard the Patang ship to kill them all. Patang chief is stabbed to death stopping him. Flint is arrested by the Royal Navy on the island, and they leave on a ship with a smallpox carrying monkey...
This is where Skull and Bones picks off, which I've yet to read.
By the time Treasure Island picks up later on, Flint has died of drink, Bones is on his last legs with the treasure map and the ex-crew (including Silver) are after him. They find him at Jim Hawkins' family's inn, the Admiral Benbow, and give him the black spot to hand over the treasure map. Bones keels over and dies after the encounter. Hawkins and the magistrate Dr Livesey take the wrapped book and map to Squire Trelawney to see what it is. Seeing it's the map to the legendary Flint's treasure, Trelawney commissions a ship in Bristol to go after it. He has a loud mouth though, and he engages the help of a big, one-legged sailor to find a crew for him. The one-legged sailor comes aboard as ship's cook. The plan was for Silver's men to take the ship after finding the treasure, but Hawkins rumbles the plan. There's a standoff on the island, the treasure is found, and Silver's men are killed. Silver is captured but escapes on a ship's boat with a bit of the treasure and heads off into the distance.
Sorry for the length of post, but that's basically what happens...
The year isn't certain, but is thought by John Drake to be around 1740ish to start. If memory serves, Treasure Island was meant to be around 1752 some years after all the Flint & Silver stuff.
