Music management without using iTunes is one of the top reasons why i jailbreak lol.
Drag and drop baby.
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Drag and drop is the simplest means to accomplish the task. Select file, "send to device xx" and done.
In 2013, the year by which technology should make things easier, if i still have to pay Apple $25 a year for my music, then upload that huge library to iTunes match costing both time and effort, then access it off the cloud, then load that crappy iTunes port for windows on my PC to access it there, then i think i am better off with a 2008 technology.
In fact i do drag and drop on my iPhone now. Because i refuse to lock myself into Apple's "ecosystem". Too bad they are clamping even harder on that so windows phone or android or BB are the only salvation in the future (guess MS also went back to 2008 by allowing drag and drop in WP8...lol)
Drag and drop only works well if your whole collection is tagged and organized well. Google offers Google Music for free because Google is heavily subsidized by Ads, in Gmail, Google, etc. whereas Apple is not.