How do you keep your game play entertaining?

adding new multifunctional buildings and stuff

I play with only one family so there's always something entertaining and absorbing to do. Because I only play these 5 household members the lack of indistinguishable characteristics, personality, and traits is not as pronounced as when rotating between numerous households and encountering sims that all seem the same. This family is also completing all of the careers, aspirations, etc., so that also keeps it interesting. I've never played a career more than once and still have plenty that I haven't yet tried.

I am a very slow player, I bought ROM at release.. and only now have my first spell caster, Mona.

I play in rotation with all the sims in the game (not the premades, but my own "creations"). Then i make their lives mingle. Then i throw some caos around: vampires, affairs... whatever crosses my mind).

I focus a lot on community matters. I have a working Council, and 5 years elections, even political parties (not played very detailed though - but I made a system involving the N.A.P.s. I also have nobility and 225 year of history for most of those families. On my website I have a profile page for all my 300-400 sims, all connected through a huge interactive family tree. I probably could have listed few more aspects, but main point is that I can play in so many different ways, it will never get boring. Whenever I need a serious break, I can work on builds or historical portraits, to fill some of those gaps. And if I want to close the game completely, I can add features to the script for my site/blog. In a way it has become way more than a game :)

Sometimes when I'm really bored, I just go into CAS for pre-made families or families I've already made, give them a sibling, parent, or child, and then play off of those family dynamics.

First, I play in my own save. It's not finished yet, but I have some good lots and a pool of decent townies, so I don't have to start from scratch.
Second, a ton of mods. I can't enjoy the game without a few essential mods, and others are making the game more fun.
Usually I'm a Rags to Riches player, I start with zero simoleons and enjoy watching my sim suffer without a house. But it became repetitive, so recently I've started a normal family. I've realized that rushed gameplay and an urge to complete everything make me bored, so I've decided to chill. My sims don't have to be ideal with a dozen completed aspirations.
Also, I've set some rules, or habits, for my sims. I try to make them act more like normal people. Choose conversation topics that makes sense (and not “ask about day” ten times in a row), brush their teeth in the morning, buy or make normal presents for Winterfest, not gift random stuff from their inventory, etc. I randomize toddlers' traits and choose regular traits based on that (fussy toddler can be mean or hot-headed, wild can be active, charmer — outgoing, silly — goofball, angelic — good, clingy — idk, insider, maybe, and for my independent toddler I've decided to pick an independent reward trait later). I choose kids' aspirations also based on what toddler skill they had developed first. Something like that.

"Simmerville;c-17738042" wrote:
I focus a lot on community matters. I have a working Council, and 5 years elections, even political parties (not played very detailed though - but I made a system involving the N.A.P.s. I also have nobility and 225 year of history for most of those families. On my website I have a profile page for all my 300-400 sims, all connected through a huge interactive family tree. I probably could have listed few more aspects, but main point is that I can play in so many different ways, it will never get boring. Whenever I need a serious break, I can work on builds or historical portraits, to fill some of those gaps. And if I want to close the game completely, I can add features to the script for my site/blog. In a way it has become way more than a game :)

I have to thank you for sharing your playstyle. I've tried to play in rotation because some time ago i read your experience about playing the game more centered in a community than in a family or a sim. I was blocked, playing legacies and getting bored too often. It has changed the game for me. I now honestly think that we get the most out of sims 4 playing in rotation.

"Ellupelluellu;c-17737356" wrote:
I am a very slow player, I bought ROM at release.. and only now have my first spell caster, Mona.

This is so interesting. I'm the exact opposite. I always dive in the new content immediately and I try to rush through everything in the new pack. I'm curious how you haven't created a spellcaster all this time? Maybe you are not into occults?

I find rotational play the most engaging. I play multiple branches of the same original family, and each branch lives in a different world and is focused somewhat on the content of a specific pack. So I'm not doing the same thing with any two households, and even though there may be similarities in core behavior they all have different careers, aspirations and different hobby activities in their homes. They all celebrate the same holidays, but each one looks different with the vampire family vs the spellcaster family vs the wealthy city family vs the country living family vs the eco warriors, etc. Basically variety is my recipe for not getting bored.