I recently started a new Rags to Riches save game for the same reasons you outline @PoppyRichards It's my favorite way to play. But, even playing that way, my Sims ultimately end up too rich, too fast and I get bored with them as a result. This time, instead of using my go to way of collecting/fishing/breeding frogs until they have enough to get an easel or planting Dragonfruit, I tried something different.
My Sim used the computers in the library to Hack, just hack, nothing else in the Programming options and she sells photographs she's taken. At first she just used her cell. After she had earned enough for a few comforts, I built her a shelter/shack made out of just a roof with a door on it. I made it a rule after that she couldn't buy anything or build a real house until she'd saved 20k for the Fabulously Wealthy aspiration milestone.
It's going slow this way, but I love it! She still lives in a shack, but her original roof home is now on top of a shack with real walls and she has her own computer to use now for hacking and a real camera. Her amenities have all been fully upgraded now too as of last night. Handiness upgrades, not particularly expensive appliances/electronics.
I'll keep her at this level until she's earned the next aspiration milestone and then she'll get the next tier of amenities that hasn't been upgraded such as a better bed, couch, etc. The only wall decorations she has are her own photographs and a couple prints from using the observatory at GeekCon. I did let her enter the Hackathon. First time I've ever had a Sim do that so I didn't know the first place prize was an expensive computer. o.O Oh well, probably not let her enter that again. lol
I have tried the Rags to Riches Extreme challenge too. Instead of fishing for a violin to play for tips though, I had my Sim collect stuff to sell. He practiced singing and entered the Karaoke contest until he won and used the simoleons to purchase the yard sale table. I love that thing! It came with CL and I believe JA has one too. He wasn't allowed to mark up his inventory, just sell items for their original worth.
Happy Simming! :)
