If the OP has a deep enough well and the static water table is low there can be a lot of pipe under vacuum.
All the drop pipe will be under vacuum, from the upper check valve almost to the pump. But if there is no hole in the upper pipes to let air in, there will be no void or empty space in the pipe to refill. If the vacuum is strong enough, I guess you might pull a few air bubbles out of the water. This could make a small air space at the top, but it couldn’t be more than a cup or so. When even a 10 GPM pump comes on, it will pump a cup in a split second, the void will be refilled, and water will be flowing out the top of the well almost instantly.
Pumping 30 seconds at 10 GPM before water flows from the top of the well means there is a 5 gallon void. 5 gallons would probably fill the entire line of drop pipe. So I think the water is draining to the static level. I just don’t know where the air is getting out.