Is this public or private? Private should work with you or have a system for this. Public will be more problematic. You should be fine to just let him out of the car in the morning but you might not be able to have someone bring him to your car in the afternoon. Your best bet would be to befriend another mom in his class who can walk him to your car, maybe in exchange for a ride home !

I know you don’t want to ask the school, but why not? You are probably paying about 100k pretax to send your child there. If you were paying this amount for a renovation, would you be reluctant to bother the contractor with questions?

I am sure there are many others who would also like to pick up in a private car. Our private has a private car pickup option where a teacher will bring your child to your car. It requires a lane for cars to wait, but I think many many parents will want to personally pick up their kids instead of relying on public transportation or taxis or Uber.

The way parking is currently on the UES, you'll have no problem double parking and just going to go get your child. Seriously it's the worst I've ever seen it, multiple cars double-parked all the time no drivers in sight. That said, you won't be the only one! I think you can just ask them how they handle this, if it's a private on the UES they likely already have a plan (I mean jeepers have you seen the pick-up and drop-offs just for 92Y preschool???)

My child’s UWS private has someone directing cars in the morning. Parents double park in the AM and PM and leave a sign in the window with their number in case someone needs to get out. I’m sure there are plenty of parents doing drop off at UES privates.