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I believe I found the problem. Just because I added songs to a playlist in my library, didn't mean they were actually in the library. Possibly the app was trying to search in the library for song rather than in the playlist. I added each song individually to my library and then to the app and so far no issues. I have closed the app and restarted the device and all the songs were able to be played. Maybe something that Apple Music should fix on their part. Thank you for the help!

Could the issue be that I'm adding a playlist as a whole rather each individual song from the library? I think I may have created a playlist, but the songs themselves were not considered to be in my music library.

My device is a brand new iPod touch 6th gen 32gb, and it's sole purpose is to play music for my summer team. So I know there is plenty of storage on it.

I went through and deleted all the songs again, then restarted the iPod, and added the songs to the app. Once the app is closed and reopened, the problem occurs again. Every song says it isn't on the device anymore.

I add songs from my Apple music playlists once they have been downloaded to my phone. The songs add and play just fine but moments later, if I try to play a song, the entire playlist says it's no longer on the device anymore even though it is. I went through once deleting every song (over 150) and redownloaded them to my phone, added to the Walkout Song DJ app, and the same issue occurred. The error is "File Not Found - [Song] is no longer on your device. Please redownload the song or chose a new one." Again, the songs are downloaded and the entire playlist says it isn't. I have the most updated version with IOS 2.3.20