I love having my sims struggle and work their way up, so to speak. I've got several families like that, that are barely making it, and occasionally get their lights or water or whatever turned off, simply because they cannot pay the bills. I've also got mods that make jobs pay less, and make bills much higher, just to make it fun.
I would get bored when I was only a generation or two into a family and they were already rich. Occasionally I'll cheat to get them a new chair or something, if they are really struggling, but I just use the money so I don't end up with too many excess funds. My legacy family had one generation where they had unexpected twins, and they lived in an apartment that was well above their means - and mostly devoid of furniture because of it lol - and they constantly had to balance raising two kids and making money (and with one spouse with the jealousy trait... boy that was a fun challenge.
Right now that same family has about 30k or so in the bank, an OK little cottage house, and we've just aged up the fifth generation to young adult, and she's a farmer/flower arranger. They've got four cats right now, too. It's a mess hahaha
