my favorites would be the big money makers, nectar, writing, sculpting, jobs that pay well, a skilled photographer can make over $1,000 Simoleons on one photograph, and nectar making does pretty well too if they're skilled up. My Sims are spoiled though, they usually come into the world telling me what they want to do through their wishes, a lot are ambitious wanting more than one job. I usually take their skills, traits, & mix them together to come up with a lifetime wish & push them toward that. I try to make them all work together.
This family is a millionaire family, they have two small children at home, and 2 have moved out.
The boy who moved out got into inventing, music and is now a director. Their daughter who moved out got into painting like her parents, & music. They are the only Sims I have to have a band. It was a family band until the 2 older children moved out. The parents did some of everything. The mother paints, sculpts, makes nectar, the father does the same, is into mixology, they are all into music and the parents have about 30 - 40 books they've written between them maybe more. They also got into photography, had rabbit hole jobs, & invested their money.
One time I left them alone while I played another family in town, and they started selling off things at the consignment store. I didn't know they knew how to do that autonomously. They have lots of perfect nectar worth $500 more a bottle and they collected thousands of year old nectar from France, exploring tombs & dive wells.
They collect occasionally and the whole family are martial arts experts. The mother & father have maxed every skill.
And I have this family who is well off, owns almost everything in town, works rabbit hole job, is a scientist, martial arts expert, almost maxed out of all skills, and does other things to make money like collecting, & gardening. He also has some nice tiberium growing in his yard, with a lot of money trees.
And then there is this couple, they both work for the police force, they are millionaires, they have a lot of money trees, own a lot of businesses, he paints in his spare time & she really doesn't have time for too much else. I don't really remember how they got all this wealth.
He's also into martial arts, and may have gotten into photography at one time or another.
Must've done nectar making too, he has the racks in that room.
I also have one or two families that became rich by winning the lottery in back to the future. The Penny Pinchers in Twinbrook is one.
The rest of the Sims I play are either comfortable or well off. I give them money in the beginning of the game but not a lot & they immediately get wishes to get a job doing this or that. I don't think they like being unemployed. If the job requires skill they wish to learn that skill, when they get that point they wish to get a job. I usually let them do what they want. There have been some, not many who I've created to do a certain thing but they didn't want any part of it, didn't even know what it was, and started sending wishes for something else & I caved & let them.
They're spoiled but they are also good Sims too. They usually wait for me to give them the command, clean up after their selves even without the neat trait & some come to the house & won't leave. I add them to the family & play them sometimes & I've even done that to burglars.
