I just want to say real quick that this is sort of based off of another challenge i found here: http://modthesims.info/t/546423
Let's set this all up now, shall we? So we have to start at the very beginning, when Wonderland first begun.
General Rules For Entire Challenge:
-NO CHEATS, with the exception of bb.moveobjects, and freerealestate (at the beginning of the game), the family funds cheat "money" may be used to set funds to a reasonable amount at the beginning as well. *No cheat needs*
-You may not save any past generation from death, or use immortal life unless I mention it and it's part of the challenge. If a family member from the current generation dies, you obviously lose the challenge if they haven't completed their goals. But if you're just doing this on your own and you want to keep going, you can save them.
-You may not renovate the house on your own if I don't mention it. That includes deleting walls, expanding rooms, moving rooms around.
-When each child is born, they get their own bedroom, make sure that it's big enough because I don't let you expand when they become adults very often.
-Do not move from the lot at any point, that includes moving the house to another town.
-Some parts of this challenge give you the option to create extra servants, DO NOT let them have relationships with the rest of the household, let them sleep in the dungeon (you may add a bed if necessary).
-And finally, this should be your active household the entire time. Do not switch households.

Generation 1: The Red and White Queens
It is the split at the beginning that is the intertwining connection in the end.

The story goes like this, the two of them founded Wonderland, therefore they're the founders of your challenge. *Note that the Red Queen is NOT the Queen of Hearts. These two are from the second Alice in Wonderland book: Through the Looking Glass, and What Alice Found There.
Rules For This Generation:

-You may use the freerealestate cheat at the very beginning to buy a size 50x50 lot (remember, this is your whole world), but no money cheats EVER. You do not have to build the house, but I highly suggest it because of the rules for it.
-The House:
-must obviously be on a 50x50 lot.
-must have no more than seven rooms:2 bedrooms, 2 bathrooms, 1 kitchen, 1 study or living room (or just combine them), 1 grand hall (opt.). If you wish, you may use the white and red color schemes and decorate like a palace. There are no limits to luxuries or decorations, for they are queens.
-DO NOT add on rooms after you've built the house, though you may expand and renovate the rooms until it's to your liking, but after you start the challenge you may not. You may not have any other kind of rooms for decorations or other skill rooms, but when the babies are born you may make each one a bedroom, but they must not share one.
-The Household:
-You must make two founders, the White and Red Queens and they must be sisters, twins are optional. If you wish to create their husbands on your own, you can go with the Kings from the chess game.
-The White Queen is all about life, so she must have a garden. She must have a combination of the Good, Loves the Outdoors, Family Oriented, or Outgoing traits. You may choose whatever aspiration you like, as long as it is not associated with mischief or evil. She does all the cooking and cleaning in the house. She must maximize her Cooking, Gardening, and Charisma skills (if you want to have her also have the Wellness and Herbalism skills that is optional, but not required). She may join a career, but it has to be either the Doctor or Culinary career. She must have one child and they must be best friends by the time the child is fully grown. She must make at least ten friends with whom she maintains relationships with.
-The Red Queen is formal and strict, and she has a temper. She is filled with jealousy because her sister is favored by the people. She must have the Hot-headed, Snob, Self-assured, or Perfectionist traits. This Queen will be all about logic and "practical" things. If you want to give her a career, she must be a Scientist or an Astronaut. She must maximize her Programming, Logic, and Charisma (writing is optional) skills. Have her make at least three friends and three enemies with whom she remains those relationships with over time. She must have one child they should not be friends because she expects a lot out of her child and is very strict.
-The Goals:
-Maximize the required skills
-Have each queen married and have (only) 1 child each
-The sisters must be enemies by the time they pass on the next generation to their heirs.
-The heirs must be friends by the time they are young adults.
-THIS GENERATION IS COMPLETED WHEN THE TWO HEIRS ARE YOUNG ADULTS, therefore meeting all of the requirements for this part of the challenge.

Generation 2: The Queen of Hearts and the White Rabbit
The two of them grew up together, and together they take the throne. Though both of them are royalty, only one plays the part, the other one disguised as a servant.

Rules For This Generation:
-You may NOT do anything weird like have the two of them have some "forbidden love"
-You may hire a maid if you can afford it, rather than W. Rabbit doing the household work
-If you wish, you may create a servant to take care of the Queen's baby, cook, and clean, but she must be moved out when the baby becomes a teen.

-The House:
-Do not remodel the home in any way that isn't mentioned, including deleting entire rooms. The castle is part of the legacy.
-Here's the exception: You may expand the Queen and Rabbit's bedrooms if you wish and add on bathrooms.
-If you do not already have a study, add one for Rabbit.
-Add a basement, this is your dungeon.
-When children are born, create a second story to the house (unless you originally built one, which you shouldn't have) and include their bedrooms and a single bathroom that's NOT attached to either one. You may put hallways on the second story or a grand entrance if you need one, but no other rooms should be up there yet.
-The Household:
-The Queen of Hearts is heir from Red Queen, Rabbit from the White.
-The Red and White Queens, along with their husbands MUST stay in the house until they die (you can cheat to kill them if you really want to). YOU ARE NOT ALLOWED TO SAVE THEM FROM DEATH with a deathflower or cheat or anything like that. They may not be immortal. If you want, you can build a graveyard or keep their remains in the dungeon.
-The Queen of Hearts inherits her mother's temper, but her rage is a "blind and aimless fury". She must have the Hot-Headed, Self-Assured, Snob, Romantic, or Active (for her love of croquet) traits.
You can go two ways with this character:
1) Put her in the Criminal career track and giver her the Public Enemy aspiration. Her goal would to be the opposite of what the White Queen's was: to make at least 10 enemies and maintain those relationships (if you do this, enemies from her childhood and teenage years will not count, though you can use people she knew).
2) This is the one I think is a little more fun. Go for the sexy, steamy Queen of Hearts image and give her the Serial Romantic aspiration. She will want to have as many affairs as possible, because she HAS TO BE MARRIED BEFORE SHE GETS INTO THIS. Any career other than a DOCTOR is fine.
Either way, you want to lock your enemies/romantic victims in the dungeon. I request trying to go into the Detective career before any other one so that you can get all of the jail cell items (or just lock them in the basement). You may not feed any of the victims, they must die in the cells ("Off with your head!"). You do not have to keep the remains, but if you do, keep them in the dungeon or in a graveyard (if you build one). As long as they're SEPARATE from the last generation's remains (royalty and peasants shall not be mixed). The Queen may not do any cleaning or cooking. She must have one child, but she doesn't spend any time with it.
The White Rabbit is the nicest guy you'll ever meet, even though he is faithful to his cousin. He does all of the cooking and cleaning (or you can hire a maid if you can afford it) but he must tend to his mother's garden on his own. He will have the Good, Squeamish, Clumsy, or Ambitious (because he wants to do his best at his job) traits. He must never miss a day of work, so no vacation days or family leave, and he can never be late. If you wish him to be employed, he must be in the Culinary, Writer, or Business career tracks. He must meet his lover at his job (this could require you to switch jobs if need be, but she must match one of the three career tracks). He must be best friends with his lover before they get romantic. He must have one child who he becomes good friends with. When you move his wife in, she must make enemies with the Queen.
-Goals:
-The Queen must have at least ten people die in her dungeon.
-She must have her child with her husband, cannot be impregnated by any other men (if you go romantic rather than evil, obviously). Must not talk to the child ever.
-She must maximize her Charisma skill.
-She must kill anyone who she becomes enemies with (through the dungeon, obviously).
-If you go the romantic route, she must leave her husband for the Knave of Hearts (the last romantic victim you choose, who must live out his life). The husband must be sent to death in the dungeon.
-The White Rabbit must never be late or miss a day of work.
-He must make a best friend who he falls in love with and marries.
-He must be good friends with his only child by the time they are a young adult
-Rabbit should master the Writing skill
-This generation ends when the two children have become young adults and all the goals are completed.
-READ THE CHILDHOOD SECTION OF NEXT GENERTION BEFORE YOU START THIS ONE
Generation 3: Hatter and Hare
Best friends forever, that's how it's meant to be.

Rules for this Generation:
-The Childhood Before:
-This generation needs some backstory to be built up, so play this part as you're finishing up the second generation.
-Hatter is born from The Queen of Hearts and Hare from the White Rabbit.
-The two should grow up best friends, they are not friends with any other kids their age, they become isolated. So Hare may not speak to anyone but Hatter and his parents, but Hatter should not talk to anyone but Hare (with the exception of possibly being acquainted to the servant who took care of him, whether that was White or someone else). So Hatter should only have one friend and Hare should have three.
-They do everything together: Eat, play, watch TV. Any activity that could include a partner, they must do together.
-They must still have slept in separate bedrooms on the second floor.
-The House:
-You may expand their bedrooms, which still should remain separate even though they're besties.
-You may also add a dining room on either floor.
-The Household:
-Hatter is determined to keep his best friend to the end, but wants to share his "mad" perspective on life with the world. Hatter must join the Culinary or Entertainer (comedy branch) careers, being unemployed is not an option. He must make and maintain relationships with at least five friends. He must have the Foodie, Insane (from being stir crazy and neglected by his mother), and Goofball traits. Hatter must master the Cooking, Comedy, and Charisma skills. He must maximize his career. His aspiration should be Master Chef or Joke Star. He must get married and have one child.
-March is a little...confused. He's funny, but stir crazy just like his good pal. He must have the Goofball, Insane, Clumsy, or Cheerful traits. His aspiration should be Party Animal and you must complete it. He does not have to have a career, but if he does it must be the Entertainer career (comedy branch). He must not get married until he's an adult. He must have one child.
-Once again when the last generation dies, their remains may be moved to the proper place. You may kill them with a cheat if you really just can't stand them.
-Goals:
(once again to just clear things up a bit)
-Hatter must maintain relationships with at least five friends.
-He must maximize the Cooking, Comedy, and Charisma skills.
-He must maximize his career.
-He must get married (at any time) and have a single child whom he is at least friends with. Must maintain good relationship with wife and NEVER cheat on her.
-Hare must complete his lifetime aspiration, which must be Party Animal.
-He must maximize the Comedy, Charisma, and Cooking skills as well.
-He must get married, but only when he's an adult and maintain that relationship. Together they must have a single child which he is friends with at the very least.
-THE MAIN GOAL is to complete all of the smaller goals, while still maintaining Hare and Hatter's "best friends" status. If at any time that relationship is anything less than "best friend", you lose the challenge.
-This is a rule, but whatever. You must not cheat relationships. You can't use a cheat to make friends or maintain friendships. If there is an aspiration reward you can purchase to maintain friendships that is STILL considered cheating for this challenge.
-This generation ends when Hatter and Hare's children age up into young adults and all goals have been completed.
-backstory preparation is in the next section.

Generation 4: The Duchess and The Cheshire Cat
Freedom is a funny thing, why do we wish to break away from all the rest?

-Backstory Preparation:
-The Duchess and Cheshire should be friends at the beginning of this generation and throughout their childhood. (good friends and best friends are not required.)

-House:
-You may expand the kitchen if you haven't already
-You may create a living room if you don't have one already
-Eventually you'll make a bedroom added on to the basement/dungeon.
-When twins are born only make one bedroom for each set, they must share.
-Household:
-You know what to do when the last generation has passed away.
-The Duchess descends from the Red line. She should have the Insane (she has a multiple personality), Outgoing, and Loner traits. Her aspiration should be Bestselling Author. She should be employed in the writer career (for she recites one of the more well-known poems in the book). She must maximize her Writing and Charisma skills. She should have one enemy (representing her relationship to the Queen of Hearts in the book). She should be married to a man and they should have a set of twins. She may only speak and become friends with the oldest child (representing her baby), the other one should be neglected by her (representing the pig her child turns into). When the twins are born (you might have to go through several children to get twins, Fertility Treatment is okay to use), she should divorce from the husband and he becomes her cook. He should sleep in a bedroom you make connected to the dungeon.
The Cheshire Cat should have the Genius, Loner, and Cheerful traits. He should be employed in any career where logic is important. He should master the Logic, Comedy, and Charisma skills. His main goal is to break away from the Duchess, so when he is married he must stop being friends with her. He and his wife should also have a set of twins. He should treat them evenly and be very good friends with them (I think you can only have one best friend, so make sure to treat them even!). He should maximize his career.
-Goals
(clearing this up a bit)
-The Duchess's and Cheshire's main goal is to each have a set of twins. If you fail to do this, you lose the challenge. Make sure you read on how they should treat them.
-The Duchess should maximize her Writing and Charisma skills.
-Cheshire should maximize Comedy, Charisma, and Logic.
-Cheshire should maximize his career
-Duchess should have 1 enemy.
-You complete this generation when all goals have been completed and both sets of twins age up into young adults.

Generation 5: The Walrus & The Carpenter along with
Tweedle-Dee & Tweedle-Dum
Twice the laughter, smiles and wins, double the trouble when you're blessed with twins.

The Rules:
-The House:
-You may add another bathroom to the house if need be, but this is optional.
-Add a workshop where you put the woodworking table.
-When they are young adults, only Carpenter and Walrus should have separate bedrooms (you are always free to have them move into someone else's bedroom that is unoccupied). Tweedle-Dee and Dum should still share their bedroom until one of them gets married.

-The Household/Backstory Prep:
-You know what to do when the past generation passes away.
-The Walrus is the son that Duchess became best friends with. He should be Lazy, Glutton, and a Snob. He is enemies with his brother (the carpenter). He should not get a job. He should master the Charisma and Writing skills. He should have at least 10 good friends. He should be out of shape. He should kill each of his good friends through the dungeon (the oysters).
-The Carpenter is the Walrus's hardworking brother. He should be Ambitious, Creative, and a Perfectionist. He should be enemies with the Walrus. He should not have had any kind of real relationship with his mother. He should be an astronaut and maximize his career. He should master the Handiness skill. He should be fit. He should get married and have one child (must be a boy, no exceptions).
-Tweedle-Dum and Tweedle-Dee count as one. They must do everything in unison. They should both be in the same career and maximize it. They should both maximize the Painting, Writing, and Charisma skills. They should stay best friends. They should be out of shape. Eventually, only one of them should get married. Whichever one you choose should have one child, who must be a girl.
-Goals:
-Carpenter and Walrus should remain enemies throughout their lives.
-Carpenter should master the Handiness/woodworking skill and maximize his career.
-Carpenter should have a baby boy.
-Tweedle-Dee and Dum should maximize their careers and master the Charisma, Painting, and Writing skills.
-Only one of Dum and Dee should get married and have one baby girl.

Generation 6: The Caterpillar and the Musical Flower
Love is love, who could deny?

House:
-If you let the White Queen's garden die, then her descendant (flower) should regrow it.
-Add plants and trees from buy and build mode to the exterior of the house (make it as whimsical as you like).
-Make another living room/lounge area. Add a piano to this area.
-If you haven't already, you may add a third story.
Household:
-Deceased should be taken care of.
-Caterpillar should descend from the Red line and have the Hot-Headed, Genius, and Creative traits. He should master the Painting and Charisma skills. He may have a career, whatever one you wish. He must have the Soulmate aspiration. He should have three friends and three enemies.
-The Musical Flower descends from the White line, she should have the Music Lover, Creative, and Outgoing traits. She should have five friends (not counting Caterpillar, who she should be best friends with) who all must have the Outgoing or Good traits (she only becomes friends with people who she believes are beautiful). You cannot edit her friends' traits. She should master the Violin, Guitar, and Piano skills.
Goals:
-Complete each character's individual goals, then prepare for something crazy.
-Caterpillar and Flower should fall in love and be married. They should have one daughter, no more and no less.
-Together, they should search for and grow a Cowplant before they have the child.
-The Musical Flower should be eaten by the Cowplant and Caterpillar should choose not to drink the milk so he can be with his love.
-This challenge is completed when their daughter becomes a young adult.
-When his daughter is a young adult, Caterpillar should be eaten by the cowplant.

Generation 7: Alice
Eternal Beauty, Eternal Life, Eternal Pain, Eternal Strife.

This is the final generation, and it is about to get more messed up. Go and look at the saying for the first generation, I bet you understand now.
House:
-COMPLETELY RENOVATE THE HOUSE!!!!!!!!! Make it look as different as ever, you may keep what you really don't want to get rid of. You can add Wonderland CC if you want. This should all be Alice in Wonderland themed.
Household:
-Alice is where the two lines meet. She should be Insane, Hot-Headed, and Childish. Her goal is to gain eternal life by drinking cowplant milk. She should make one best friend. She should master the Charisma, Writing, and Painting skills. She should not get a job, she wants to be forever young. She should sacrifice her best friend to the cowplant and drink the milk for eternal life.
Goals:
-Have Alice maximize the required skills.
-Have Alice never fall in love.
-Alice should make one best friend and have her fed to the cowplant (you might have to have her move in)
-This challenge is completed when Alice drinks her first sip of the cowplant's milk.
I HOPE YOU ENJOY!

This is a bit of a challenge, literally!
May I ask you if I can make this to my youtube channel?

This is an amazing challenge, and I'm currently working on Gen 3 (The March Hare & The Mad Hatter), who are children. The only complaint I would make is that I wish it was a full 10 Generation Legacy Challenge. I would suggest adding other interesting characters to the ones you listed, such as: The Doormouse (somewhere around March Hare and Mad Hatter's Gen), The Jubjub Bird and The Jabberwock(y), The Gryphon and The Mock Turtle, The Lion and The Unicorn, The Red and White Knights, Bill The Lizard, The Bandersnatch, and Alice's Sister (alongside Alice). Fantastic challenge