I don't really enjoy playing pre-made sims (they're just not my sims, so I tend to care about them somewhat less), so I never start out with a rich family. Any time I start a new game, I start with paupers.
Also, one of my favorite things in the game to do is to design and build houses. I absolutely despise nearly every pre-made house that came with the game or any of the expansions. Typically, they're ridiculously small, cramped, have only one bedroom and bathroom, and are simply impractical in general. Thus, I tend to start with the largest empty lot available in the town and design a house for the family to gradually build. Did I say I start with paupers? I'm sorry...I meant utterly destitute.
These houses have ranged in size and often differ radically in general architecture, but one thing they all have in common is that they are extremely spacious and tend to be lavish. And have lots of bathrooms. As a result, even when I end up with a family that is rich, it's usually net worth and they tend to not have a lot of money in their household funds. If there's money laying around, it gives me leeway to change or add something.
Another thing I tend to do is create a family cemetery. One of the first things I do is change a sizable vacant lot to a graveyard lot, making it available for purchase by the family. Community lots that are completely undeveloped tend to be extremely cheap, and it's a lot of fun building them up from literally nothing.
And now, with the addition of Late Night to my Sims collection, coupled with the fact that most LN buildings don't fit well into cities other than Bridgeport, I have the option of changing a vacant lot (or even creating a new one) to one of the new LN lot types, buying it and having them build that particular establishment totally from scratch. I have yet to have the opportunity to do this, though, as I haven't had the game long.