The problem I faced a long time ago was trying to Max out all the skill Levels, reach the top of the career branches, getting Gold, or whatever to have "Perfect" events. Making my sims wealthy. Then I remembered, In real Life, I'm not at all Career driven, and my aspirations are pretty simple
Also, this is My Story, the Sims are just empty husks, to fulfill certain roles of characters. I don't have to conform to "the Lore of the Sims" I can play this game my Way. you know I don't call things like So this was a major realization to have more fun.
So at Birthdays, Weddings, Events and Active Careers, I do what I want to have a successful event, so getting Bronze, Gold or silver means absolutely nothing.
I don't strive for sims to reach top level career promotions.
My Sim, Ursula Hudson Originally, I wanted her to own a 5-Star Restaurant, but while she was humble she was fine with that, until she met her ex-husband, He will corrupt her in many ways, to be more ambitious and at the same time try to "domesticate" her. and that is why he is going to be her ex-husband.
Same thing with other sims, My Police Sim all he wanted, career wise, was to be a Detective. So Becoming Senior Detective, will be his highest promotion.
For me to have more fun I had to strip the game of all Premades, and Create and rebuild Sims, Homes, and Lots, and Fully Customize the worlds to my own needs. It really helps make going to Places like working at the Hospital, Police Station, or Science Labs more enjoyable. Seeing familiar faces, instead of random townies, wearing random outfits and such.
Using Mods, CC, and Cheat to your absolute disposal. especially if you are a story teller, and a control freak like me, It's okay to make your sims wealthy from the get go. I have Several characters who are Mansion Barons and Fabulously wealthy, and they have several more aspirations to get, but to Start us off, I wanted my Characters to have certain Skills, and backgrounds in order before I start playing.
Other Challenges, I think helped is the History Challenge and Supernatural Aspect. because It domino'd into the Generational/Legacy aspect.