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Also, to add on to what AtomCrafty is saying about the three Milton ending achievements:
For Deal with the Deceiver, there's another path. When Milton opens with "Oh you came back to keep me company", answer "What's best for me", "Precisely", and "Friends are just another instrument". In the next dialog, answer "Yes, if it suits me, I will co-operate", "It changes nothing" and "I would be elated". Then, you have an easy way in the next (penultimate) dialog to get on board with Milton. If you do, you can only get Deal with the Deceiver in the final dialog, but get some extras as well.
For Silence the Serpent, what's listed here is one way to banish Milton, but there are other paths as well. In any case, once Elohim bellows out "Enough!", you've already chosen this path, so all you need to do is finish the conversation.
1 - you need an axe (required to complete p 5)
5 - you must choose "Look for Wood" if you have an axe
Assuming you play through the worlds linearly and collect everything as you go, Milton should initiate a conversation after you've completed world C5 (at 25 stars) that starts like this:
"There you are. You kept me waiting. I finally put my finger on what was bothering me."
Make sure to not agree with Milton in this conversation, otherwise the next time you speak to him you will be locked into an alternate conversation that only allows you to get the "Deal With The Deceiver" achievement. If you do oppose him, then the next conversation (where you need to follow the options per the description) should start after finishing C6.
Also yes, the order of all the people freed in Road To Gehenna is the same, no matter what order you solve the puzzles.
Apparently using CRObar in B7 to break down a secret barrier (Needed for Cat ending) also counts towards the achievement.