@LJLove I moved your post over to the Android space.
Playlist doesn't download for Offline Mode:
I've enabled a trace on your account to help us better understand what's happening.
For this trace to be useful, we'll need you to run through our troubleshooting steps: Troubleshooting Offline Listening
Let me know how it goes.
Unable to search for songs in a playlist:
While there isn't currently a way to do this, I recommend upvoting this existing thread if you'd like to see it added to the service: Ideas: Ability to search and sort within personalized playlists
I hope this helps.
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