HELP: Tips For Rotational Play

Well, I can give you the rules I go by, but know that there are about as many ways to play rotationally as there are rotational players. There's no "right" way to do it.

My save is a Prosperity Challenge, which is a set of rules first thought up during the TS2 era. The TS2 rules were much more involved than TS4, but basically it boils down to starting a completely blank save and creating a randomized number of households, which you then proceed to rotate through on a set schedule. Over time, the numer of households grows as the Sims marry and have children. (I started with 5 houses back in 2015. I now have close to 30.) Like I said, the gameplay rules are pretty involved but I can give you the gist of how I set up my save and how I keep everything organized.

Setup:
1) Either download a blank save file, or evict and bulldoze all pre-made lots and families so you're starting with all empty lots. In the options menu, set your aging to "active household only".
2) Roll a dice. That number (between 2 and 6) is how many households you will create. If you roll a 1, roll again.
3) For each household, repeat the dice roll. This is how many Sims you will create. Again, if you roll a 1, roll again.
4) For each Sim (you guessed it!) roll a dice two times. The first number represents the Sim's age. 1=toddler, 2=child, 3=teen, and so on. (If you end up with all children and toddlers, you can re-roll, since the game won't let you create a household without an adult.) The second number represents the Sim's gender (odd for male, even for female).
5) Use a Sim randomizer site (I use createarandomsim.com) to choose aspirations and traits. (There is a very long guide in the rules about how to roll for aspirations, but this is so much faster...)
6) Names and appearance are up to you. Relationships are up to you as well, as long as everyone in the household is related in some way. (No roommates).

Even if you don't choose to go this in-depth with randomization, I would recommend creating your own families to start off. By starting everyone fresh out of CAS together, you give yourself an equal chance to find the story for each household. (The randomization options also can force you to play with family structures and traits you may not have chosen otherwise.)

I play each family for 7 days each. This is easy to keep track of (I just go Sunday to Sunday) and as an added bonus it lines up with the calendar weeks in Seasons. No matter how you choose to set up your rotation, I would recommend having some sort of a structure. I've found that having this in place keeps me motivated to play through the weeks with the families I don't love as much because I know that the ones I absolutely love are just a few lots away.

As far as keeping track of them, I have my play list pretty well memorized now (I actually set up their houses in the order that I play to make it easier). I do, however, keep a list each round of Sims who are due to age up into teens during that rotation, so I can think ahead to who should end up with who. (Because the youngest child of each family inherits their parents' house, I've found that I can reduce the number of new households by strategically matching up my playable Sims rather than bringing in townies.)

Another kind of odd thing that I do to keep track of my Sims is to assign each house a naming theme. These themes range from the semi-normal, such as characters from a TV show or movie, to the bizarre, like brands of medication or types of fish. That way, I can instantly tell which Sims grew up in which house.

Finally, since you mentioned that you typically play a family for multiple generations, know that you can do that with rotational play as well. The 5 houses that I started with have since spawned 4+ generations of descendants, and the family lines have become so interwoven that half the town ends up showing up every time there's a wedding or a birthday.

Again, this is just what I do. Just do whatever keeps you excited and engaged.

Good luck!