Set Them Free!G 40

Ravenscar Keep Door:
DO NOT open this door last. This achievement is known to be very glitchy, even after the latest Title Updates.

Wear every piece of the prisoner outfit in front of the door.

Prisoner Bandana: In a chest hidden in the small rock maze near the garden. To get to the garden, go down the left pathway when facing the bridge to the entrance of Ravenscar Keep.
Prisoner Top: In a chest located in the second cell on the left in the left wing of Ravenscar Keep (requires the quest Prison Management for Beginners to be in progress or complete).
Prisoner Shackles: In a chest which is accessed by vaulting off the rocks to the right of a hole in the wall of the garden area (the same hole which leads to the Demon Door).
Prisoner Trousers: In a chest at the end of the cemetery (requires the quest Undeath Sentence to be in progress or complete).
Prisoner Boots: In a chest behind the gallows over the fallen piece of fencing. To find the gallows, head in the opposite direction when facing the bridge to the entrance of Ravenscar Keep. (Tip: It's in a chest near one of the General Turner diaries.)

Millfields Door:
This door requires you to make yourself as ugly as possible. There's 2 parts to the door's request. One is to become as fat as the game let you (so when you look at your character's bars, the Fat bar is in the red), which you can easily do by visiting pubs and buying out as much alcohol as possible. Sometimes, the bar glitches and even though your character is the fattest it can be, it will still be in the green, but that's alright. The second part is to wear ugly clothes. The most easy ones are the Pyjamas of the opposite gender or the Chicken suit.

Mistpeak Valley Door:
Coop with another hero (can be done local with a second controller and a local profile), and either propose marriage, or do all the available positive interactions (which requires at least one player have the required expression chests unlocked in the Road to Rule), in front of the door.

Brightwall Door:
You must have a child (either by sex or by adoption) and perform a positive interaction with them in front of the door.

Sunset House Door:
You must simply become King/Queen.

City of Aurora Door:
You must have either 100% good or evil morality. Going for good is more easy, if you have money. If you've done Tough Love, it's very likely that you also chose all the good choices in your judgements. Transferring big amounts of money from your personal funds to the castle treasury is also a quick way to bump up your morality.

Mourningwood Door:
This door will unlock only when you have opened the fifth level chests for Ranged and/or Melee weapons in the Road to Rule.