In your original post, you posted a screenshot showing the object browser. In that object browser, the Popup window... notice how it is in a grey font rather than black like everything else? That means that, at the time of the screenshot, it is not "Visible". Everything is present, but that popup is not actually visible. So, that means that, when you click on the menu to generate the popup, before you click on an individual menu item, you need to wait for that popup to be Visible.
So, your code should include, after the click on the menu, something like
Aliases.menubarApplication.menuitemAssociate.popupAssociate.WaitProperty('Visible', true, 2000);
This will wait up to 2 seconds for that popup to actually resolve as visible before you attempt to click on the individual menu item.
The clue is the "Overlapping Window" error.... there is something that is overlapping what you're trying to click.... and I'm guessing that it's because the popup isn't fully resolved yet. Give the above a try.