I'm having scenario trouble too, but for a different one! The "difficult" one of Exploring the Night! I can check off every other item, but the "stay up for 5 days in a row" never goes past 0/5.
I tried in a new save, had that problem, then tried in another game. It never shows that my Sim has stayed up even one night let alone 5.
I've had Sims stay up 10 days in a row, the second one was a Sim who had loads of Satisfaction Points so I stocked him up on Sleep Replacements, and 2 Sim weeks in, without having slept, he's still sitting there at 0/5 for that goal.
Very frustrating. Yes, I played it completely mod-free both times. The second time, I went ahead after way more than 5 days of no sleep, and added in MC Command Center because my Sim had already aged up to Adult, and I wanted to rewind him so he could go to University.
I'm about to just close down the scenarios and forget about it because it appears broken.