All i'm suggesting is that for your "punch hole" theory to reflect the shown outcome, each plane would have to descend at "X" distance from the airport to coincide with the movement of the cloud cover, therefore, "Hypothetical Scenario 1" would be favourable for achieving a "grouped appearance" as shown in the photo.... "Hypothetical Scenario 2" would be favourable for achieving a "Queued appearance"
Are we on the same page??
Somewhat. There are multiple different scenarios that could end up with the same result, depending on the speed and direction of the cloud layer, the cruise altitude of the planes, the actual location of the plane, and the angle of descent. It's not hard to imagine several that end up with the image seen.
Note that the wind is not at all necessary. You could easily get the same result with zero wind, but that's unlikely.
I've been looking into your Dec 3 photo. TWCobra suggest military planes, but let me suggest another explanation, wich I think fits your observations very well:
Quantas has a regular scheduled service from Sydney to Brisbane, the north flights are even numbered 502,504,506 etc. Your trails are labeled as being laid at 7:50, 8:15 and 8:45 on Dec 3, 2012.
Quantas flight 506 arrived at Brisbane at 8:20AM, and at about 7:50, was entering a high altitude hold with descent over Gold Coast Airport at 37,000 feet. That matches one of your flights.
Quantas flight 508 arrived at Brisbane at 8:54 that day, and at about 8:15 was entering the same hold/descent.
Quantas flight 510 arrived at Brisbane at 9:18 that day, and at about 8:45 was entering the same hold/descent.
Here are the flight tracks for those three flights, viewable in Google Earth:
View attachment FlightAware_QFA506_YSSY_YBBN_20121202.kml
View attachment FlightAware_QFA510_YSSY_YBBN_20121202.kml
View attachment FlightAware_QFA508_YSSY_YBBN_20121203.kml
So I'm suggesting it was not one plane flying around, but THREE planes, all of whom flew the same circuit, but one after another. Each plane was descending as it moved off into the distance, and would stop leaving a trail, then the next plane would come in and start leaving a trail. So it seems quite plausible that you could lose sight of the (no-trail) descending plane, and then see the newly arriving plane shortly thereafter.
This also might shine some light on the holepunch photo, as an example of what happens to real-world flights sometimes. These three flights, all of whom planned to take the same direct path, ended up being delayed a bit, and all descended through (say) 20,000 feet at very different positions, but within an hour of each other. Here's a different perspective on that: