How to Recover lost downloaded songs in Apple Music?

When I download my playlist with 400+ songs on it and go to the location Apple Music says it sends the songs to, many of the songs and even many albums are missing. Adding said folder to Windows' media players, they only report back about 200 songs have been downloaded and a quick properties check shows the whole folder only contains about 300 files total (even with hidden files on). No amount of me redownloading the songs will get the rest to show up, even when Apple Music displays as downloaded. This also happened to me when using iTunes 12 on Windows as well. Is there anyway I can get the rest of the songs downloaded without having to manually find them on the internet?

[Re-Titled by Moderator]