I see headphones the same way as I view sportbikes.
An $8000 sportbike can outperform (in a lot of ways) cars costing eight times as much. However, there are definite drawbacks to the bike -- limited passenger capability, limited carrying capacity, elemental exposure, higher demands placed on the operator, riding gear required, and lack of inherent stability. But for the same price as a very pedestrian econobox car, you can purchase a ZX-14 capable of quarter mile runs under 10 seconds right off the showroom floor, or a literbike that is equal to full on racebikes from a few years ago. The value is amazing.
Same thing with headphones. Grado SR60 is what, $70? But of course there are drawbacks -- headphones are solo-only, you're tethered, the headphone chassis can make noise, the bass doesn't have the same impact, etc. But again, the value is amazing.
But I find my opportunities to listen to home speakers are few and far between compared to my opportunities to use my car stereo, work headphones, and home headphones, even with a house. And even then, sometimes the speakers are just too much, and I want the quiet intimacy of headphones.