I've upgraded from 188.8.131.52 with what appeared to be not much of an issue.
I see how the files are linked differ somewhat, as it appears to use PHP to re-direct the download link to where the file is actually uploaded.
For example, when copying the File URL from a particular download, then pasting into a browser, it'll find the file.
If you follow the Download link from the front-end, it just adds the Download Endpoint + Endpoint Value to the site's root URL and does not find the file.
I feel like I'm looking at this in too much depth, and the solution is very simple but I'm overlooking. Any advice here would be greatly welcomed!