Speculations
This whole post contains spoilers you have been warned:
1. I choose Tuttle because he knows about the north grove. If the Lord thought it that important then it is something that the right hand man needs to know. I think regardless of who you picked, Tuttle will end up leading the family.
2. Squire Tuttle is not seen arriving at the Wall, only seeing Snow do his work. I imagine he will come to the wall but what will that mean for the story as he will be bound there. He has to either leave before joining or become a deserter which will lead being a foil of the deserter/thief that I sent to the wall.
3. The non-Forrester handmaiden is a spy for Cercei. The coal boy is one of the Spider's "little birds".
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Comments
My speculations: The maester is a traitor, he acts really shifty after certain interactions (when telling him about the secret and when talking about giving up our wood). Someone also let's ramseys man in if you meet at the gate, so my bet is it's him.
The coal boy is 100% a spy. It was so obvious from the start. I guess he could be working for Little finger or one of Varys little birds.either way, he's spying.
The Maiden: didn't trust the maiden friend we had, could easily be gathering intel for cersei. During the discussion about marrying for power etc she already revealed she would do anything for power. This could easily mean betraying Mira
edit: after replaying and telling the maester obout the north grove and then telling your uncle you told the message to the measter(he is clearly trustworthy since lord gregor forrestor trusted him esspecially) he says: The maester is the last person I would trust with this information. So.. initial hunch I had confirmed?
It's funny cause I refused to trust anyone in Kings Landing apart from the characters from the show. I knew Tyrion could be trusted, and Margeary had some loyalty to her hand maiden. But everyone else just felt shifty, the coal boy obviously had ties to some spy network, probably Varys. The hand maidens in Kings Landing usually have ties to Cercei, and with Cercei having a deep mistrust to Mira I knew she would have someone try to find out if she is a traitor, so I refused to trust the hand maidens.
If the maester is indeed a spy then he has to have a good reason. I think he is taking the whole "Sacrifice for the greater good routine" with good intentions but bad judgement, again I'm not wholly convinced but he is definitely shifty and I wouldn't trust him.
Every Maester's loyalty is questionable. They've got conspiracies within conspiracies, that lot. But helping the Boltons wouldn't be one of them, given Roose's propensity to kill the unfortunate sods sent to the Dreadfort.
The in-game codex says that the Maester "hope(d) to be assigned to the Eyre" however after Jon Aryn's death he was assigned to the Forresters. So there is some substance to the idea that he is the one working in concert.