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Right now, features does not support two menu items in the same menu that have the same path.
It is due to the identifier for the menu items being menu-name:link_path, limiting it to only one of such a combination.
I first though of adding a parent path to distinguish, but that'd break if they have the same parent (for example, I've put two+ user/register links in a menu with different destination='s [which isn't stored with the link_path]).
So, in such a situation, when exporting the menu item, it needs to determine a unique identifier that will be able to used also when loading that menu item, and that needs to be used whenever there is 2+ of the same menu item. Now being that multiple features could be in play, ugh!
Though, that gets complicated further due to needing to be able to update the feature, for example if what was the unique identifier is changed. Well it could be seen as a new item, the old item is very unlikely to be removed if 'customized' = 1comes into play.
I have given a thought that this situation might be best by letting the user choice the identifier in some way, like by only supporting the situation by .info file addition. but that is confusing for users that only create a feature via the UI.