How do I upload songs larger than 200MB to my iPhone with iCloud Music Library enabled?

Apple targets its products for the mass market consumer many of who find using an on/off switch a technological imposition. If you have a playlist on your computer and on your phone, but modify it slightly on one, which is iCloud supposed to obey? The solution Apple has selected is iCloud trumps all. If you want Apple Music or Match your syncing is to iCloud. But then iCloud has its limits too, such as not blowing a fuse on file storage. Your average consumer has 3 minute music tracks, not 200MB files and if you browse this forum you will see many posts about things people on the edge want to do, but they aren't the 98% market. While Apple might be able to program direct syncing as an option to add individual tracks to an iPhone it might make things horribly confusing for many users. 😝

You may find workarounds such as splitting up your large files, or recoding them to a lower bitrate.

Voice your suggestions to:

http://www.apple.com/feedback/itunesapp.html

That is one of the eligibility restrictions for uploaded tracks with iCloud. I guess Apple understandably does not want you to upload 25,000 x >200 MB files. iCloud does not work for all scenarios.