Hi KDubSD. This is a friendly board and you normally would have gotten some replies right away but October is a ways out and you are better at advance planning that most. There is talk of a get-together in October, and there will be many people going up besides the regulars, so you will have little trouble finding company. There is also the Mt. San Jacinto Hiking Club
https://www.meetup.com/Hiking-Coachella-Valley/and they have lots of trips up Skyline in the fall. I'll be going up myself at least a couple times so I'll keep an eye out for your posts. In any case, welcome! Hope to see you out there on the trail.
z