I'm in a similar situation, though I'm taking a more progressive approach. I currently own a Shure SRH440 headset and a Xonar STX. I'm upgrading to a Mr. Speakers Mad Dog headset (with 1/4" plug), Ceentrance HiFi M8, and an iPod Touch. All this scores to me as I gain portability, an improved amp/DAC combo, planar headphones, and an iOS device (I can finally give the big, power-hungry PC a rest more often).
Maybe in a year or two I'll upgrade to a balanced Alpha Dog headset. A year after that, I'll likely move to a more private living space where I have full intention of running loudspeakers. In that situation, I'd like to buy a Schiit Gungnir and line it out to a mixer with balanced outputs for both speakers and headphones. If I HAD to get other stuph after that, I may trade the Dogs for an Audeze or some other higher-end, balanced, planar headphone, purchase the Gungnir's other half (the Mjolner) to drive them, and trade the HiFi M8 for something more portable. Music CDs take priority, though.
Technically speaking, using balanced headphones makes sense. A two-channel home audio setup will typically include a receiver wired directly to flanking speakers, with positive and negative wires to each. A balanced headphone system simply miniaturizes that setup, maintaining separate grounds for each driver.
Definitely spring for the balanced rig I say. Mind, the Mjolner doesn't work with single-ended 'phones according to the FAQ on the product webpage. Had I not discovered the HiFi M8 or balanced headphone audio, I'd probably just get a Schiit BiFrost/Asgard 2 combo and be happy.
EDIT: I ended up buying the balanced version of the Mad Dogs instead. That driven by the HiFi M8's 4-pin XLR jack should keep me happy for awhile. It's also the cheapest, full-power balanced rig that I'm aware of.