ITunes help? ITunes purchases won't sync with iphone?

So I have an item (an radio show-aka a "song") that shows up in my itunes as purchased, but if I go onto my phone it doesn't say that: It just tells me how much it is like I have not purchased it. I've checked in my purchased files, and it's not there on my phone. I can't sync my phone to my itunes at the moment… Is there any way to get that item onto my phone? Would re-buying it actually charge me?

I don't understand why so many rely on "syncing" to put music on their device.

I never sync any of my devices to put music on it. Instead my iTunes is set for manual management of music and video. I almost never have problems putting music on my iPod and obviously much fewer than those complained of in questions like yours which are posted here in the thousands - including loss of music to put songs on my iPod.

Manual management is just clearly superior in every way and it works on iPods, iPhones and iPads both new and old. I've tried it on first generation nanos, iPod 4, iPad 3 and iPhone 5