An update from my trip...
I went from October 4-7, attending all four nights. Started every night in the New York Stay and Scream area, and hit the houses in this order:
Silent Hill
Gothic
House of Horrors (cut through Sting Alley and take the sidewalk to Central Park for a shorter walk)
Alice Cooper
Penn and Teller
The Walking Dead
Dead End
Thursday, 10/4: Crowds were light due to the rain and the plan worked perfectly. Had all the houses done by 7:30, and even scored a solo run through Alice Cooper! Longest wait: 10 minutes for Dead End
Friday, 10/5: Again, crowds were light due to the
threat of more rain, but it turned out to be a nice night. Plan worked perfectly, all houses done before 8:00. Longest wait: 15 minutes for Dead End
Saturday, 10/6: Much heavier crowds tonight, but the plan still worked well and I even scored another (mostly) solo run through Alice Cooper. Longest wait: 45 minutes (!) for Dead End
Sunday, 10/7: Worst night for crowds, plan didn't work well at all. I managed SH, Gothic, AC, HoH and TWD by 8:15-8:30. Penn and Teller and Dead End were at least 30 minutes each and I was on a tight schedule that night, so I used Express later on P&T and had to skip Dead End entirely.
Longest wait: 30 minutes for The Walking Dead
I later found out Sunday was "Hospitality Night" and anyone in the hospitality industry could get tickets at a cheap price. Sunday has always been fairly busy in my experience, but it was never this bad.
It seems Columbus Day weekend is becoming a very popular time to go. If I return next year, I may switch to the second weekend.
I hope this info was helpful to anyone going to the event soon!