Blowing the air out just seems like your on borrowed time before a tiny leak, lets all your air out and it fills your main drain back up with water.
I have released the main drain valve after closing it to see what happens. Yes, you are correct. Water does come gushing back in. But, in the spring, when I open the MD valve, the water does not behave in the same manner. The air will compress as it cools, so some water will get in the bottom of the pipe, but there is normally still enough air to keep the water below the frost line.I believe this only happens immediately and technically it is not lost air, but air that compresses during the cold weather.
I do not believe if a valve fails over time, the water will surface back. Air compression takes time under ground vs. the outside temperatures, which probably means that the process is over time, maybe as long as a month. With car tires, you could wake up to literally a flat tire because of overnight drops. I have seen a 5 PSI difference overnight, not because of air loss, but air compression in tires. Then again, my elevation is at 163 ASL (above sea level), while the bottom of the drain is at least 10 feet lower. This is all about physics and a little complicated.
The Cyclone is powerful enough to move most, if not all the water to 8'. Once air is trapped in there, eventually as the air compresses and cools, slowly water will fill back in the piping, but you will still be below the frost line. The idea of having water freeze, expand and contract does not sit well with pool owners.