I would like to note, right off the bat, that I use a modified version of the Build A City Rules. This reflects my playstyle, my preferences, what makes sense to me, and what can be best translated into historical terms.
Getting Started
1. Hood. Create an empty and clean hood neighborhood using mods like antiregen and clean hood templates. Place appropriate hood decor. Since we're starting off as a rural community, trees, brush and maybe a few farmland tiles are appropriate. Feel free to add any decor for natural aspects, such as ponds, rocks, beach waves, etc.
2. Families. Create 1 founder family and 4 settler families for a total of 5. These sims should be teens, young adults, adults and elders (since the life of a settler might be too difficult for young babies, toddlers and children). I like to assign each family a trade of sorts (i.e. Founder family is destined to be in politics and/or law enforcement; settler family 1 might be dairy farmers; settler family 2 could be apple orchardists; settler family 3 could be farmers; settler family 4 might be woodcutters/carpenters; settler family 5 might be fishmongers). Specific personality details are typically randomized unless I have a detailed family concept in mind.
3. Money. I'm not a fan of the way money is calculated for families, so I've decided to take a different approach. I use a class structure that includes poverty level, lower class, middle class, and upper class sims, with a range of wealth. For each family, I use a random generator which indicates how much money that family will start off with. If I have a very specific concept in mind for one of my sim families, I might override this and instead randomize the roll to fall somewhere in between the sim's chosen class tier. I use the familyfunds cheat to give them money.
Upper Class | $45,000-$70,000
Widdle Class | $25,000-$45,000
Lower Class | $15,000-$25,000
Poverty Level | $5,000-$15,000
4. Lots. Not every sim gets a massive lot when moving into the neighborhood! Their lot size depends on the lifestyle they're going to lead, the architectural style they will follow (which can change from generation to generation), and the wealth at their disposal. A family who will have a dairy farm, for example, might want a larger lot because they will need room to have a barn and a field for their cows, calves and cattle. A farmer might need a larger lot as well, but perhaps not as large as the dairy farmer, so that he can start a crop with room to expand as his own family grows. A very wealthy merchant might want a medium-sized lot so that they can have a decent sized house with room for a home business on the first floor. Keep in mind: you can always use lot adjuster to make the lot larger (and charge the sims per square) at another time if they find their lot is not big enough, as long as their is room around their chosen space to expand.
5. Move In. After placing a lot for each family, move them in. These sims should be living in tents for the time being, until their houses can be built. Before this can be done, the lot needs to be cleared of all trees and shrubs (which I simulate by placing chopable trees, which will be used for fireplaces, stoves, campfires, and the actual building process). Before you do anything else, teleport the playable families you just played onto your lot, and talk to everyone. Really get to know them!
6.
Rounds. Now it's time to play in rounds. A round is simply a cycle of playing all the families you have created in a specific order of your choosing. When you have cycled through them all, a round is completed. I prefer to play my families for a full week - Monday through Monday - and simply add new families to the end of the original rotation list. I also use an extensive RoS that gives me specific objectives to achieve during that round, or as many rounds as needed. Whether you play this way is completely up to you, as long as you obey the rounds rule!