For my playthrough, I think it was in the low 300's before I got it:
The brunet girl in the shorts by the pool.
Then running to the girl that walks by her garage directly across the Cul-de-sac.
The guy trimming the tree in the yard over.
The lady in the back patio enclosure.
The guy cleaning the pool at the start.
I had to do a literal 360. God I hate this game so much, but one of most difficult missions is behind me.
It took 55.40s to do. I was booking it trying to get to that last guy and not surprise him. I got close to getting the mission 3 times and I always surprise the last guy somehow.