OFB made it so money is pretty easy to get. If my sims are too broke, I usually have them run a business for a while until things get better. I don't make all my sims very wealthy. I like having some differences between families. I even keep a few "broke" families around.
I've noticed that the less shortcuts I take with a particular sim lot, the more satisfaction I seem to get out of it.
Using the Insim to me isn't always cheating. It's one thing to give your sims badges they didn't earn and quite another to use game code to get your sims out if a stupid situation that you didn't really intend. (like when they get stuck maybe).
The game is what you make it. If you are bored and your sims are all pretty much doing the same things all the time; if you aren't happy with that it's your own fault!
I let my sims take risks, I always try to have at least one doing as much in the game as I can find for them to do. Be a vampire, be a werewolf, become a plantsim or a zombie (uh do i need to mention that I have all the expansions?), or be rich or poor.
Having said that, ideally my neighborhood would be balanced with enough different families doing different things so I can match my mood when I play and the game never gets too boring.
Well I think I've answered the original question plus some maybe.
Dang! Coffee is good!