I do it if I want to and I don't feel badly about it. I generally do so in order to set up a household in a certain way so it generally is for "story-telling purposes". I have some households with less money.
I used to play households that would try to build up money over the generations from poor to wealthy but now I rotate between households at different socioeconomic levels instead of focusing on one family as it tries to acquire more. I don't judge the other play style but I think it's how I used to play the game most of the time so I'm just interested in more variety.
I suppose I create challenges by flipping between households. My natural inclination is to make high-achieving, high-earning sims so actually switching households is a way for me to counteract that tendency and to create more interaction. A high-achieving parent might have a child who marries someone "from the wrong side of the tracks" while someone from a working class background might marry someone wealthy.
The most boring household I currently have is my royal household (Von Haunts) that is happily married with a perfect little heir. I've got no idea what to do with them besides sending them to vacation in Sulani. Their palace is stunning (thanks gallery) but if a royalty pack would help me to liven things up for them, I'd be game.
Hugo Villareal was more interesting to play as a YA because though I played him as an aristocratic heir, he was also shy and nerdy, so he had his own personal struggles. He's an adult now and married for love but is otherwise pretty reclusive. The Von Haunts' lives are completely breezy. I can figure out what to do with them. I would like them to be involved in more charitable works which I could probably do with the club system.
Anyway, I pretty much only use cheats for story purposes and to create variety but I don't feel bad about it. I view the cheats as tools to apply when I want to. It's not like I'm cheating constantly to make things easy. It's just that not all of my households are rags-to-riches. I've cheated traits for a sim occasionally for story-telling purposes such as to make a villain.
Off topic but Hugo Villareal's son is a totally spoiled "bad boy" who is very good-looking and acts nothing like Hugo. I think he'll get sent off to military school to shape up (and maybe fail at it). Watch out, next generation. The little Von Haunt prince is like ... a Disney character while Hugo's son is someone who would end up in a lot of tabloids.
