It's not a plain analog headphone socket; it has an optical line out as well.

http://i.imgur.com/V9QbH7I.jpg http://www.apple.com/shop/product/H7048ZM/A/belkin-6-digital...

It's also a reasonable quality DAC and more than good enough to do work on the move with. Your statement makes no sense, unless you measure "proness" by the girth of a connector?

Neither is monitoring via Bluetooth.