@DinoNuggetsRUs
You could ring the school and just say "Can I please check where parents are allowed to park doing drop off.. and see what they say. You don't need to mention where you are parking. Could even say that there seems to be some confusion." Then you'd know one way or the other.
It' s probably fine to watch him walk to the door but as others have said it might be something to do with the parking space.
Could you get Spicy a little trolley toy of some sort to push, we used to have one with toy cubes in it, with a little handlebar, which you could whip in and out of the car much more easily and they could push/walk with you and DS in front? Cos it sounds to me like Spicy wants to be more independent and might enjoy that more. (I had trouble getting them into the car, and getting them out of the car again.. so I do understand)
You say often in your posts that you are pushed for time, or cutting it fine.
II hope this doesn't sound patronising, (because I've been in your situation) but I think this might be making things more fraught for you, including finding parking spaces etc.. and also maybe why your Spicy is being tricky.
It's completely understandable and probably there's lots going on but maybe it would be time to get a regular routine going where everything is laid out the night before... a go bag by the front door, and getting yourself up and ready first a bit earlier, breakfast mostly laid the night before Think about what things are holding you up in the morning and see if there's a fix if you prepare in advance. Eg (if Spicy won't eat breakfast in time take a small snack with you)
You'd have time to keep things calm, they'd get used to the routine and you'd feel less flustered and more in control which in turn would pass to them. It would give you so much more confidence, especially if there's a dirty looks brigade.
It's still only September. Everyone will soon start to settle down. I had a Spicy, they needed lots and lots of running about. Ignore the mean girls. Chin up. It will get better. Also if you do go in with DS, you'll get a chance to see some of the other mums, who may also have a Spicy themselves and can set up playdates etc.
Enjoy this time, its hard work but there's happy times to be had as well x