See my updated macro above that properly handles the Page Thumbnail panel being open.
@jipnet, @JMichaelTX - This is great detective work! Good job!
I admit I’m not completely versed in what you’re doing (and frankly, I don’t want to be 
), but if there’s some way to package this up with some instructions, one or both of you might want to post something in the Macros category. I’m sure there will be others who will want to use it, once they see that this type of automation is possible for Acrobat.
Also, I’m would think that some of this type of automation would work with the non-pro version. So you might want to indicate that also.
Again, good job. It’s like watching a good mystery movie on TV.
Happy to do so but am not sure how to post that. I agree, spread the wealth. Digital communism…
Mine is a bit buggy: I get error messages (about Macro cancellation) sometimes, not all the times, but even when I do it works. JM’s may be more secure.
Did you arrive at 200/100 by trial and error or did you use “Get” to arrive at that? (I don’t get “Get” yet.)
Note that in my version you don’t have to specify a pixel location: once the menu displays, it’s 8 down arrows [your idea] + return and it’s done.
I used the Mac screenshot tool ⌘⇧4 to select a region.
Drag it from the top, left corner of the window into the Page Thumbnail area, and read the location shown on the screen. Press ESC to cancel the screenshot.
Enter that location (which is relative) in the KM Mouse Move Action.
You're just lucky that your mouse happens to be in the right area. 
If the mouse it NOT in the Thumbnail area, then the context menu won't be proper.
That's why I thought you two might want to work together.
Also, there's nothing wrong with an incomplete solution. The more you can document what might go wrong, the better.
However, let me say this from my experience: If you try to do too much, you may never end up posting your results because it's just too much of a PITA. In my opinion, I'd rather have a half-working solution that tells me "caveat emptor", than none at all.
@JMichaelTX knows all about this - more than I do, so I'll let him and you take it from here.
It may even be that this topic is enough as is, with perhaps a change to the topic title. Again, @JMichaelTX is actually the expert on how and where to post things on this forum.
I'll be glad to post my example macro in the "macro" category. It's already setup as an "example".
@jipnet, if you are using my macro, or some form of it, please let me know how it goes. I'll wait to hear from you before I post it so I know it has had some real-world testing/use. Please check the "Solved" checkbox on my post if it solved your problem/request, so other's will know it worked for you.
Thanks.
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OK< I will keep trying it out. I just set up your macro, and it is working with no errors; and you are right, I was testing it from the same place before, which was misleading. Will let you know how it goes.
Incidentally, my Page Thumbnail area is 211 down, not 200, but 200 seems to do the trick; 100 is well within the range, though technically my entry point is more like 67. So I guess apps tend to have soft tolerances for these things. It will be interesting to test this on an iMac (using an Air at the moment) to see if the dimensions matter. Can’t do that for another 3 weeks yet, when I will get back to my office location again.
I’m pretty sure you have it right. I never would have thought of the if/then command; I’m new to this kind of level of detail using KBM (and am not sure I want to get much deeper—trying to save time, not create more distractions, fun as they are!). Thanks again.
While the above Macro works OK as posted, here is an improvement to select the menu item by name, rather than by position:
Yup, that works as well. (In my case it’s “Page Labels”)
BTW, how are you inserting the balloon comments in your (I assume) png’s and other commenting symbols? This doesn’t look like it’s from Preview.
tx
I use SnagIT.
If you do a lot of custom screenshots, videos, and/or animated GIFs, and make great annotations very easy, SnagIT is a great choice. Some consider it too expensive at $50, but that is a license for both Windows and Mac, on all of your computers.
I've used it for over a decade now, and really like it.
Yep. I've used it at least that long also (mostly on Windows until recently). It's like an old, sometimes cranky friend.
Thanks for the tip.
You could also open the menu behind the little Options icon 
via UI AppleScript.
At least with Acrobat Reader DC this works; I cannot test it with Acrobat Pro DC:
tell application "System Events"
tell application process "Acrobat Reader"
tell window 1
tell group 1
tell group 1
tell group 2
tell group 2
tell group 1
tell group 1
tell group 2
tell menu button 2
perform action "Press"
end tell
end tell
end tell
end tell
end tell
end tell
end tell
end tell
end tell
end tell
end tell
No. It just opens the menu. (The same as the mouse click, but independent of coordinates/screen dimensions.)
I see. Let me try that next. tx!
The script will just open this menu:
The other actions in your macro —before and after that— are still necessary.
But, as said, only tested with Reader DC.
Acrobat DC is the Candy Crush version of Acrobat. You used to be able to assign keyboard shortcuts to functions that didn’t have them.
Have you tried seeing if you can use an Action (in Acrobat) to apply your page labels? Here’s the Adobe Help on using the Action Wizard: https://helpx.adobe.com/acrobat/using/action-wizard-acrobat-pro.html
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Sorry for the delay. That’s a clever way into the problem, but not out of it. Once you create an action it is indeed possible to call it up with KBM through Acrobat’s menus. But selecting that action from the “Action List” seems elusive all over again.