That sounds like an awesome way to play @Ashkevron ! For my challenge, I let my sim buy the smallest empty plot of land (they need a 'home' address after all), build nothing there and then used a cheat to take away all his remaining simoleons. His first money he made by selling fish he caught and small paintings he made on the easel next to the water (I'm playing in Windenburg). Most of that money went to meals at restaurants (wanted to prepare him for the restaurant business, so he had to eat there as well ;) ), he slept on the benches in the park and he used the bathroom at the gym for his other needs. My sim also has the dance machine trait, so his socializing (and dancing for fun) he did at the nightclub in Windenburg.
After a challenging time, and after his painting skill got better, he was able to buy a second plot of land and is building his restaurant there. Tough going, but he's got the exterior warehouse up now and restored, and a few dining tables and the other necessities to open up his own restaurant. At the moment, he was finally able to build a mini apartment on top of the restaurant, with his very own bedroom and bathroom. :) Now it's onward to upgrading the restaurant, making it look nice, adding a nightclub there on the side and making his own apartment on top bigger and more comfortable, while at the same time still keeping up with expenses from running the restaurant and paying his bills from his home lot. Have had so much fun already with this save!