Hi Karl,
I am not at all sure if I am understanding the problem here at all.
For years now, when adding a link to whatever text you have on a page (just a regular text gadget), you have been able to add a link to internal pages, external URLs and files in the WA File structure.
From a file perspective however the pain has been that as you add a new file to the directory, you have to add a new link to the page.
What is really required here is a Library Gadget - where you can link to all the files in a directory and optionally any sub-directories.
See: https://forums.wildapricot.com/forums/308932-wishlist/suggestions/8825557-document-library-gadget
Now an additional idea that I have implemented for about 3 years now is that you can add files to a forum article (maximum of 20 files).
So I have a Meeting Minutes Forum and each year I start a new article (members can only read and cannot even comment). Than as we go through the year, I just edit that article and add in the most recent applicable file(s).
I also do the same thing for my news letters (save the PDF file of these into the applicable post).
From an administrative perspective - just edit the post, take the add file option and select the file from your PC. save the post. Under the covers, WA stores these files in the File system (there is some funky naming system).
My email to members when a new file is added just tells them that whatever has now been posted and here is the link to the actual forum.
I have found that getting members to subscribe to the forums is a total pain and of course WA does not provide any support for Admins to subscribe members to a forum (only to change or remove a subscription once a member has subscribed)

This feature would also allow me to link to content that's stored in Files. For example, I need to generate pages that include links to our Zoom events and recordings. I create an HTML page, but then need to copy and paste the content into an existing WA page. It would be much nicer if I could just update the content in Files.

As much as it would be ideal to have a link in a menu to link to an external page, it's not best practice from a usability perspective. Also search engines may penalize your site if you have lots of menu based links that redirect to external sites. This is how spam farms tend to work and how they try to game search engines.

Best practice is to have a page on the site that links off to the remote page, but have the menu load the page locally on the site instructing the visitor to link to another site.

It sounds in principle like it is a good way to "shortcut" the 2 step process of a local page linking off to another page, but it is best practice to link off a page, rather than linking directly offsite on a navigation menu. Remember when visitors use your website they expect navigation menus to take you to another page on your site rather than offsite.

Great idea. Simplifies many issues.

The lack of this feature is a major oversight by WA. We migrated here a couple of years ago from a less sophisticated club based web portal where we could point a menu item to a URL. We were amazed we can't do this here.

I would like to be able to add menu items that link to any specified URL, including pages within the site. While I think good design often eliminates the need for duplication, sometimes a page needs to be linked to in multiple locations for user-friendliness. For example, if a main menu item has a drop-down (secondary menu), sometimes people don't realize they can click on the main menu item and only look in the drop-down options. A main menu item of "Become a Member" could link to the same page as the drop-down option "How to Join." Also, it'd be nice to be able to add menu links to different anchors on a single page, and to be able to link to files, e.g. PDFs, so that we can list items such as our Bylaws in the menu.

Is there anyway to make menu items point to an external site in a new window?

I have used the redirect but I would like the page to open in a new window.

BTW, ideally I think these menu items should be somehow visually differentiated so that site visitors are not unexpectedly thrown to some other place.