Hi Ned!
Attaching files to pages is preferred when you have a few attachments that are related to the content of a page. Users might not typically search for these files on their own, but they are useful in the context of the page. Some examples might be screenshots on a page or a few files linked on the page.
The File list blueprint is useful when the files are the main content. It's meant to be used when you have a list of files to share with people. As an example, you might have a set of Microsoft Office templates, or a central location to store all your team presentations.
It may help to consider that the attachments in a file list are still just attachments on a page. For example, if you have a "Presentations" file list, all files on that list are attachments to that same "Presentations" page, displayed in an Attachments macro. The benefit of the file list blueprint is that these lists are easily generated and accessible from the sidebar.
So to sum it up: Regular ol' attachments on a page are good to supplement content on a page, and file lists are good for sharing lists of files easily accessible from the sidebar. If you have any use cases in-between, you can also include the Attachments macro on any page to feature a list of attachments.
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