Ok, so, the deal for both teams.
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Team Jock (Prison):
Obviously we need to know who is going. The procedure will be this-
1. Get in through the front. You can try to fight or talk through. Thea will be there but she reckons the Yeomen there are increasingly subverted by Aquila. They won't fire on Thea but they will fire on her Ladies-in-Waiting so it;s no good her going in alone.
2. Get to the control room. Thea knows the way but there are likely to be issues, depending on how step 1 went.
3. Recover the LIWs from cryo sleep. This has two complications- first, getting them out the prison system. The carbonite blocks are inside the ice mountains themselves and moving them is discouraged. Move them out of the approved order and the whole system will go into lockdown.
4. You then need to revive the ladies- the carbonite blocks move too slowly for an escape, and might be damaged. Of course, the yeomen will be firing at you as you do this. They'll all be suffering from hibernation sickness too.
5. Get out of there. Probably no talking through that one
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Team Nerd (Library)
You need to consider:
1. Getting through the city to the library without arousing suspicion. Sneak it or bluff it. Don't fight it.
2. Be able to operate in the Library without suspicion. Sneaking keeps a low profile but you cannot do that AND research, so this bit needs the most preparation
3. Research the library systems. Many skills useful here- you already noted Languages as one but there are others.
4. Find something relevant on Adelmo. Straight rolls might get what you want, but good ideas will make the rolls easier.
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Both teams will rendezvous in the city afterwards.