Source (Please check out the original source, it really helps the makers of the challenges): http://www.modthesims.info/showthread.php?t=537800  

THE SIMS 4 SETTLER CHALLENGE

Your sim has decided to be one of the brave heroes throughout history who travel to the loneliest places on Earth to find a new home. Your job is to survive and create a thriving colony in the middle of nowhere.

GOAL
To build and to populate your colony. The challenge is over when you've lifted all restrictions.

SETTING UP
-Set lifespan to normal.
-Aging must be on.
-Create a couple in CAS (young adult or adult). They are your settlers. Pick their traits and aspirations randomly (you can use dice, random.org or this trait generator: ). Choose which one of them you're going to control.
-Bulldoze all lots in the world. Your sims are settlers and there are no other people living in the colony yet. You may leave one starter house and buy that lot for your sims, or you can build a completely new house or download one from the gallery.
-Choose the starting era for your settlers and choose the furniture, clothes, decorations etc. accordingly. For example, if you want to start in the Wild West in the 19th century, don't buy a television. (Besides, your colony won't have electricity in the beginning in any case.)
-You must use all or almost all your money building and furnishing the house. You can also buy up to three books and one pack of seeds. The point is that you must not have any money when you start the game. If you run out of things to buy for some reason, use a money cheat to reduce your money to zero.

RULES
-You may only control one sim. That sim is called the heir. You will control several heirs during this challenge, but only one at a time.
-There may only ever be one heir at a time. You can freely choose who the next heir is and you can decide when to start playing the next heir, but once you've decided, you can't change your mind and go back to playing the old heir. If you start playing the new heir while the old one is still alive, the old one is not considered an heir anymore.
-The new heir must be the previous heir's child.
-If the heir has many children, all those children except the future heir must move out when they become young adults.
-The heir may marry and move their spouse in.
-You may not age sims up days before their actual birthday.
-Cheats, mods or hacks that give you an advantage over a person who doesn't use them are not recommended.
-If you want to make this challenge easier, you can use one helper (the spouse / sibling / parent etc. of your heir). The helper may do simple tasks (such as repair an object, water plants, cook a meal, feed a baby), but you shouldn't control the helper too much - only a couple of tasks a day. If you don't use a helper, you may notice that the inactive sims in your family won't do much (or any!) work autonomously, which does not feel very realistic in a hard-working colony.
-Traits and aspirations are always randomized when a baby is born or a sim ages up. You can use any random trait generator (e.g. or ) or just roll dice. Exception: You may choose the traits and aspirations for the child if either of the child's parents has any of the following traits: Family-Oriented, Patriarch, Mentor.


POPULATING THE COLONY

Yours is the only family living in the colony in the beginning.

Rules for adding families:
-When you are allowed to add a family, create them in CAS or download them from the Gallery. Roll a six-sided die or use random.org to determine the number of people in the family (between 1 and 6).

Different ways to populate the colony:
-Have babies!
-You can use your Charisma skill to persuade people to join your colony: You can add one family for every sim in your family who has reached level 6 in Charisma.
-You can also attract people by hosting great parties. You may add one family for every type of party for which you've got a gold medal. You can only invite people who live in your colony to your parties, you can't invite homeless people!
-Improving the services and the infrastructure in your colony will also make people move into your community. You may add one family for every community lot you add.


RESTRICTIONS AND HOW TO LIFT THEM

School
There is no school in your colony. You must prevent children from going to school.
Requirements for lifting this restriction:
-There must be at least twelve people living in your colony (your family included).

Medicine
Hospital births are not allowed and woohooing may always lead to a pregnancy (roll a six-sided die or use random.org first: 1 means you need to pick the interaction Try for baby instead, and if you roll 2-6 you can just pick Woohoo). You can always choose to Try for baby if you want to.
Requirements for lifting this restriction:
-There must be at least three different community lots in your colony

Electricity
There is no electricity yet. You may not use the computer, the TV, the radio etc. (You may use the fridge, however).
Requirements for lifting this restriction:
-There must be at least four different community lots in your colony AND one of the sims in your current family must have 6 skill points in Handiness

Careers
You may not have a normal job as there aren't any companies or infrastructure. Careers are therefore not allowed, but you may use other means to earn money (painting, collecting, gardening, fishing etc.)
Requirements for lifting this restriction:
-There must be at least five different community lots in your colony
-There must also be at least thirty people living in your colony (including your family)

Higher education
There are no possibilities for higher education in your colony. If you unlock this, you can always choose the traits for your sims when they age up or are born.
Requirements for lifting this restriction:
-You need to lift the restriction School first
-To lift this restriction, one of the sims in your current family must have the trait Genius and be at least a young adult.


ADDING COMMUNITY LOTS

There may only be one community lot of each type (ie. one café or restaurant, one pub or bar, one library etc.). One heir can unlock and add only one community lot during their lifetime, unless they have one or several of the following traits: Business Savvy, Genius, Ambitious. In that case, they may unlock and add one community lot per each of those traits that they have during their lifetime.

When a community lot has a certain cost, you can either pay for that lot or try to fill the other requirements, in which case you won't have to pay anything. If you decide to pay, just use a money cheat to reduce your money by the required amount.

You don't have to add all the community lots listed here in order to win this challenge. You can choose which ones to build.

A church / a wedding venue / some other nice place for your colony to gather and meet each other
This should preferably be the first public building or venue that you create. There are many nice choices in the Gallery (under General), but you can also build it yourself. Just remember not to make it too modern!
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have 6 skill points in Handiness

A café, a restaurant or a bakery
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have 6 skill points in Gourmet cooking

A pub or a bar
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have 6 skill points in Mixology

A museum or an art gallery
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have 6 skill points in Painting

A library
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have 6 skill points in Writing

A concert hall or a lounge
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have 6 skill points in Guitar, Violin or Piano

A park
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have 6 skill points in Gardening

A nightclub
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have 8 friends outside the current family

A gym
Unlocking requirements:
-Cost: 5000 simoleons OR your heir must have fully completed their aspiration (it doesn't matter which aspiration he / she has)

Random events – optional

If you want, you can roll a random event every Sunday to keep things interesting (use dice or random.org).

1 The spring festival makes people romantic. Add a new baby to a random family in your colony (Manage Worlds -> Household Management -> Edit sims in CAS).

2 One of your current heir's children feels that they cannot bear the responsibility of building a colony. That child isn't allowed to become an heir. Select the child randomly. (If your heir doesn't have children, nothing happens.)

3 A flood destroys the house of one family in your colony (pick randomly) and you want to help them. Move them into your house. You may move them out after one week if you want.

4 Problems with the building permit office. If you can raise your Logic skill by two points (unless it's maxed already, in which case you succeed automatically) in the next 24 hours, you'll be able to convince them that your requests are rational and nothing happens. If you can't raise your Logic by two points, you may not build anything before next Sunday.

5 Fire! One of your community buildings has burnt (pick randomly). You may rebuild it using your money if you want to, but it will cost 5000 simoleons. If you don't want to rebuild it, bulldoze it.

6 Unrest on the border! All young adult and adult sims will have to leave the house to help EXCEPT the heir, because the heir must take care of the internal affairs of the colony. Move the other adult or young adult sims out to another lot. Every day after this, roll dice or use random.org to pick a random number: 1=The war continues and one of your sims is killed (pick randomly) and will not return home after the war, 2= The war continues, 3= The war continues, 4=The war continues, 5=The war is over, everyone can come home immediately (move them back in), 6=The war is over, everyone can come home immediately (move them back in).

7 The autumn festival makes people romantic. Add a new baby to a random family in your colony (Manage Worlds -> Household Management -> Edit sims in CAS).

8 A casanova moves into the community, sweeps one of the female sims in your family (young adult or adult) off her feet and knocks her up. Pick the female sim randomly. That sim may even be your heir if your heir is female. Instructions: Create the casanova in CAS (if you haven't already), move him into your house and make him Try for baby with the selected sim. You can then move him out if you want to.

9 Your Mister Casanova is at it again! This time a female sim from another household gets pregnant. Pick the female sim randomly. Instructions: Create the casanova in CAS (if you haven't already), move him into the female sim's house and add a baby to that family in Household Management.

10 A family asks if they may move into your colony. You decide. If you say yes, create four sims in CAS and move them into your colony.

11 Oil has been found in your colony. Use the cheat Kaching or some other money cheat to add 2000 simoleons to your family funds.

12 Gold has been found in your colony. Use the cheat Kaching four times or use some other money cheat to add 4000 simoleons to your family funds.  

NOTE: I DID NOT COME UP WITH THIS CHALLENGE. PLEASE, ONCE AGAIN, CHECK OUT THE ORIGINAL CHALLENGE CREATOR AT THE FOLLOWING LINK: http://www.modthesims.info/showthread.php?t=537800