I do this challenge all the time in TS3 (in my opinion definitely the best tittle for it thanks to open world) but I also have a homeless family in TS4. However, it being my first in TS4, I'm still learning how to have the best experience (and actually want to kind of restart it because of this). I developed my own rules for TS3 and am still doing that in TS4.
I have this tradition to always do this challenge with Harper and a daughter who starts as a toddler, that's because it was such an hilariously obnoxious combo with Harper's less agreeable personality (and distaste for children) and having to look after a child sim while being ill equipped to do so. TS4 iteration is basically a direct copy of Harper from TS3 (though way more tame when it comes to autonomous behavior). They always need to travel together, so no abusing TS4's self-care systems.
So far, in TS4, I have developed some rules I want to put into practise the next time I do this. E.g: Don't use any reward traits. I did this time cuz I really wanted to try the "always welcome" trait but I feel it's way too good for this. I think I'm gonna download a mod instead which makes it so good friends (and close relatives) don't mind "inappropriate" behavior. That would still be sufficient amount of challenge because Harper, with her obnoxious personality, has to actually go through the effort of befriending sims. I'm also thinking going with the "your lot doesn't exist" route, a.k.a not doing anything more permanent in there, not even gardening.
"somewhsome;c-17942565" wrote:
4) Sometimes I set a rule that my sim can't travel outside of the world they "live in". The hardest challenge was when I was starting in San Myshuno in winter. My sim had no money, no one was grilling anything or even eating from the food stalls (you can steal that food sometimes haha). I think only Night in the Town saved me.
@somewhsome Really liking this idea. I need to do this the next time. I mean, when allowed to travel between worlds it gives you an easy way to avoid bad weather and such and use all types of facilities. Your idea can add a nice dose of realism too because, well, how are they even able to travel around so much if they have no or very little money.