https://gyazo.com/0872dfb312f692f9ed2c17978d0af4c9
No matter what iTunes will NOT let me sync a playlist to my iPhone. The link is the prompt I get when I try to apply 'Manually Manage Music,' NO I DO NOT WANT TO WIPE MY PHONE.
I've only found one other way of exporting the playlist—going to the playlist, pressing the '…' then add to > iPhone, however that simply does nothing.
iPhone 5s, iOS 8.4.1, Latest iTunes?