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Went through everything in the Walkout app and had to re-download several songs.  Will check again tomorrow to see how things are.

That sounds like an issue in Apple Music itself as the Walkout Song app has no capability to remove songs from the library... 

Are the affected songs actually from an Apple Music subscription or are they ones you have added to iTunes manually?

I'm on a free subscription with Apple Music for another couple weeks.  I have been testing and a pile of things were gone this morning that were there yesterday. I have turned in the sync function and corrected the ones that showed some sort of error in the playlist while waiting at appointments.  I'll have to check it on the iPad when I get home.  I left it running and on wifi when I left.  If I read the info correctly, anything I changed on my phone will show up on the iPad

the email address you posted is kicking back an address not found message when I send to it.

That error message is triggered when a song in your music library has its cloud flag set and the device is not connected to the internet.

Can you try opening the 'Walkout Song DJ' playlist in your music app with internet connected and tapping the red download arrow in the top right corner to force download of all the songs?  Verify all songs have the downloaded indicator visible, then retry your offline playback test.

I'll go through this and see what happens.  But it's not that the song isn't downloaded every time.  There are songs that are completely gone from my library.  I have to look them up again in Apple Music, add them to my library, and hit download again. 

iPad Air 2
iOS 15.3.1

Sent email

I could even go for sliding the volume control to the left which may be easier to do given the available real estate than making it larger.  That would move it away from the buttons to the right of the slide.

I would love to see the volume slide bar have more real estate.  sometimes I need to make an announcement between innings after we started music.  I'd like to be able to throttle the volume back, say what I have to, without starting the song over.  My fat fingers usually mute the volume and unmute it a couple times before I can get my finger on the slider to push the volume down.

BTW...I absolutely love this app and what we are able to do with it.  Been trying to sell other schools on it.

Is it possible that the new device does not have enough space for all the songs to be downloaded at once?  I know if you have the 'optimize storage' enabled in the settings app, music section, the device will remove less recently played songs to make room for new ones.   If it is a space problem, you may want to check if you have the audio quality set for lossless in that same music section of the settings app.

It is a 64 GB device and I've used just less than 10 GB total on the device.  Seems there's actually under 1 GB of actual music.
The error reads:
Apple Music Not Connected
[Song Title} is an apple music song in the cloud and your device does not appear to be connected to the internet.  Please find an active internet connection, open the Apple Music app and download the 'Walkout Song DJ' playlist so the songs can be played without internet connectivity.

I have used the app a couple seasons on an iPad.  This season I had to migrate to a different iPad (Air 2).  The OS version is 15.3.1.   I am having an issue where songs I have added to my Apple Music library, and downloaded, just disappear.  I go to select the song in the Walkout app and get a message that basically tells me I'm not online and need to be.  I go to Apple Music and find that the song has disappeared from My Library.  I re-add, re-download, disconnect Internet and everything is fine.  This has happened enough that I'm going through my entire Walkout app before every game to test each song and re-download what I need to.  Last game, I did this, closed the app to reset what had already been played and once the game started, we had songs disappear again.  It's not the same songs every time.