He explained in a previous post that subsequent updates of many of his applications would mess up his carefully crafted categories, so he prefers not having to deal with that.

In that case it really is a question of preference and against that there is no argument. However, regarding the automatic cascading menus vs. More option, the reasoning for how it currently operates is based on functionality.

I remember what I changed that made Grid Stacks on the taskbar sometimes open behind open windows.

I was having a problem with older games that didn't run at desktop resolution minimizing to the taskbar immediately when launched from a Grid Stack. I found that if I selected "Disable all animations" under the General Preferences tab, the game would launch without a problem. I also found that created the problem of Grid Stacks on the taskbar sometimes opening behind open windows.

I stopped using Grid Stacks on the taskbar for that reason, but I forgot why I did.

I also came up with another solution. Place the Dock with the Grid Stack in front of the taskbar just to the left of the System Tray area. Make it "Always above other windows", and make it "Auto-hide for maximized applications when always on top". That solved both problems I was having.

And BOOOOOM, just like that you caused me to know about and fix two bugs. The first was a Grid not coming to the foreground if animations were disabled and the second was the Grid being forced to the foreground when playing the HIDE animation (which is why the game got minimized when launched from a Grid Stack).

Ah but the point is his categories get messed up when there are updates to many (?, sic!) of his apps because he is using the folders in Program Files - i.e., a folder view of exes etc. Whereas this would not happen with the links copied from the Windows Taskbar - at least, it never, ever happens here.

Sure, there's no argument against preference. And exactly the point - functionality first.