Thank you everyone for all your detailed and thoughtful responses! I am amazed that you would take so much time to help me out 
***WARNING*** The following is a terribly long winded response to everyone’s advice. Skip it if you have better things to do.
I wish I had time to respond to each one individually, but instead I’ll just go ahead and tell you what I’ve taken away from your collective advice (some of the changes I’m making are from advice I received on another forum).
Game play Changes/Comments
Side note: The “session zero” has already been in progress for two weeks via facebook messenger. The conversation concerning characters, rules, dynamics, etc has been going on at length nearly every day. This session began with me submitting 8 different potential settings/plots. This island adventure that I have created was their top pick. Had I known more about learning to be a DM before-hand I probably would have chosen a premade adventure, but quite frankly, I’ve invested way too much time into this endeavor and I’m just going to go with it at this point. The players are also in agreement that this game is kind of a throw-away game, just to get our feet wet. We hope that this campaign will be relatively short. They are not even sure they want to keep their characters for the next game we play and if the session doesn't grab anyone, we will start again once we have a better idea of what everyone wants.
One of the main things I keep hearing is that the PC’s need to know each other before we get started. This was my initial request for my players, but they couldn’t agree on intertwining back stories so they just decided to be strangers. After reading your posts, I decided to insist that they figure it out. I suggested various voyage activities that may have provided potential bonding experiences. They are still working on it but they have agreed to figure it out.
Another reoccurring piece of advice you guys keep saying it to start our characters at level one. For some reason I was under the impression that starting at a higher level would make it easier for me to plan more interesting encounters and this is why I recommended level 3. I’m afraid it’s too late to tell my PC’s to redo their character sheets for level 1 and I’m worried they will become vexed. Especially since our game is on May 7th and all our players are adults with full time jobs. Not to mention, I would have to go and rebalance all of the encounters and I’m not sure I have time for it.
In response to those who worry about my designing my own monsters, I should have been more clear. All I really did was adjust the HP, AC, or damage slightly to make them more appropriate for my player’s level. I recycled the templates for similar monsters as best I could since I don’t trust myself to be able to design a balanced monster right now.
As far as some people being worried that I’m railroading by PC’s or that I’m not truly prepared for alternative possibilities, I guess you’ll just have to trust me that I really mean it since I don’t have time to type out PLAN B, C, D for every scenario. Though the most common issue I see people worrying about is “what if they don’t go with the Tongu tribesmen? What if they fight instead?”. My plan in that event is that Akira (the translator) will eventually seek them out and relay all the information they would have gained at the village and attempt to enlist their help to rescue her sister. She will vouch for her tribe in getting the PC’s off the island. This will bypass the village scenes entirely and I will be forced to move the campaign along to the second act where they set off toward the hag’s hovel. I have those encounters ready to go just in case. I have more back up plans prepared and I will rely on improvisation a fair bit, but I hope I’ve demonstrated that I really do mean it when I say that “I am prepared for the PC’s to go a different direction”. Though I’ve never played D&D I’ve been a play-by-post role-player for 11 years, so I do have an inkling on how to improvise, though admittedly not under timed pressure. We will see how it translates.
I think I’ll go with someone’s recommendation that the tattoo will provide three instances of poison damage, fading a bit each time it is used until it disappears entirely. Either that or it will provide resistance against the Yuan-ti’s “suggestion” ability. As for the condition to receive the tattoo, how about something simple like walking over hot coals. I could use a constitution check to determine how stoically/gracefully this is performed. It may provide a bit of amusement and role playing fun.
I told my PC’s to be prepared that this island will not have any shops (it is terribly primitive), so purchase any necessary items from their starting gold before-hand. I will narrate that they escaped from the ship as it crashed in a lifeboat and that they have their starting gear with them. To clarify, the trading post where the merchant line comes through is not a town. It is little more than a bay where the Tongu meet the tradesmen every month. It would be difficult (but not impossible) for the PC’s to find on their own as they would have to circle the island coast which would be quite dangerous. Once they get there, they would have a nearly impossible time bartering passage off the island because the traders will not be willing to sacrifice their trade relationship with the Tongu who may hold this over the PC’s heads to get them to help. I doubt it would ever get to this point as my players are the ones who decided upon this adventure.
Story Changes/Comments
I decided to take some advice on the captain. I will not automatically kill him off anymore. I will make him a bit of a prick and a coward. He will warn the PC’s of how perilous this island is and how they must get to the trading post with his help. When the snake encounter begins, he will run and hide. Once the PC’s kill it, they will immediately be confronted by the Tongu (who will take them sleighing the snake as an omen that Lono has chosen them to defeat the Yuan-ti). The captain will warn he PC’s not to go with the Tongu and will lie about their wild nature (in truth he is afraid to be left alone and he is also afraid to go with the Tongu because he knows someone will recognize him as a slave trader who has harvested them from this island in years past). I expect my PC’s will choose to go with the Tongu, not respecting the word of this captain (If not, Akira would eventually approach the group on her own and recognize the captain, revealing his dishonesty to the group if they refused to go to the village).
If they go with the tribe, the captain will follow, having no better option. He will be recognized and the Tongu chief will want to execute him. The PC’s will then have the chance to argue his case if they so desire. I think this will provide good conflict/RP opportunity, not to mention they can make some persuasion/intimidation/deception checks
I need advice on Akira
Here is the rundown on this character. Let me know what changes you suggest.
Akira is a hunter and spend much of her time in the wild. She had a very close relationship with her younger sister despite their opposite nature. That is, until her sister became engaged to the chief’s son. Out a jealousy and a fear of abandonment that Akira doesn’t quite understand, she seduced her sister’s intended and is now secretly pregnant with his child. Racked with guilt, she is motivated by more than heroic loyalty to rescue her sister from the Yuan-ti.
This character will be used as a guide/translator. Though she can fight, I don’t intend on her being overly helpful during the encounters. She may not even be present if the encounters take place on holy ground where she is forbidden to go (she is very superstitious). Her main purpose is to make the story more interesting and provide RP opportunities and dilemmas….. such as the following…
1. The hag they meet will reveal to the party that Akira is pregnant and demand the child as a price for her help (see hag lore for more info). If all members refuse, then she will make a different request which will involve them destroying something sacred and beautiful in the forest. Both options will be terrible as the paladin’s back story includes a proclivity to protect mothers and their children while the druid’s back story is that of a forest guardian. The hag will revel in the discord this moral quandary sows. They can either comply with her requests, try to trick her, or attack her. Their choice. Side note: regardless of what they chose, in the end the hag will double cross them and attack Akira to attempt harvesting the child.
2. At the end of the second act, I intend for Akira to be captured by the Yuan-ti while she is out hunting. This will provide the opportunity for the party to be heroic rescuers toward a character they may actually care about, and it will also remove her from the possibility of stealing any spotlight in the third act. Or they could let her die, it doesn’t really matter to me.
What do you guys think?
***One more note about Akira***
I assume many of the people reading this are men. I happen to be a woman and I am running a game for all male players. Is Akira’s story too… I don’t know… girly/soap opera-ish? Being the only female at the table I am super self conscious that my players will be tempted to roll their eyes at some of my story telling themes. What do you think? Is Akira’s story too corny for men to be interested in?
