When I had nothing more than base game, WA and HELS and after playing a couple of games with sims who had become quite rich the ease of getting money was bugging me so I decided to make a poor virtuoso mooch sim to see how easy it would be to live off nothing but tips and mooched food, I built her a scruffy one room shack with no cooking facilities and surrounded by weeds, hay bales and junk, the house cost enough to take almost all her starting cash, she had just enough money left to buy a guitar.
Well the first few days were okay, she played her guitar constantly and mooched food from people, she actually ended up eating better than most of my other starting sims, then once she could play for tips I sent her into town to do so, I had no idea about performances affecting tip money and she never left that guitar alone so had racked up a huge number, her first tip session she got 10,000
A few days later Sherman Bagley asked her to move in, and then Jon Lesson, two of the richest men in Riverview, I just gave up then and decided trying to be poor was a total fail, and this was pretty much with just base game if you discount WA.
In some ways though it depends on the game I'm playing, more often than not with my self sim she starts as a lone teen, on an empty lot sometimes with a house, trying to juggle school make her money last, keep her needs up and everything is not easy because I don't allow myself to use the shortcuts, I like the challenge, seasons added another challenge because of the weather, she's either a crispy critter from the sun or she's a popsicle from the cold, of course once she graduates and gets a job it all gets easy again and unless I have a new LTW to finish the boredom sets in, that's why I like the dynasty challenges, I like a goal to work towards and even this late in the day with gen seven a kid it still throws curveballs at me.
So yes it can be too easy, which is what drove me to start playing challenges but they have made it even easier in some ways because I now know far more tricks than I used to, like the guitar performance thing.