This was a pretty cool challenge! I used the childish trait/Barfly, it must be awfully hard without that!
You might want to mention in the instructions somewhere that the game will not count the days passed for you. I really don't understand why the stat section will tell you totally useless info like how many times your sim went to the bathroom but it doesn't say how long your sim has been alive. I didn't realize that was the case until I was done so I was unable to score my finished challenge (I played with the aging off so I can't even try to calculate by my sims age). it's my own fault for assuming, but I'd like to save someone else the sickening feeling I felt when I realized that info was nowhere to be found.
Another thing I found out is that if your sim is sad he gets the option to call the sadness hotline, which raises his social. Is that allowed in this challenge? I did it once early on but decided it probably wasn't legal.
Great challenge, I hope you think up some more!