Sure, go for it (headphones). I think you would be remiss to not explore planar-dynamics and electrostats - though planars are generally harder to drive, and electrostats even require their own special dedicated amplifiers (that you can't use for anything else!). I love moving coils in cartidges and speakers, but in headphones it’s slapping this mass around (coil glued to a former glued to a diaphragm) right atop your ears, and (IMO) they tend to produce far more listening fatigue and danger at higher volumes. Also, even amongst other moving coils, I never liked Sennheiser 800’s series. The older 580 / 600 / 650 series has far better tonality, if a bit less detail.
Headphones for sound control
I'll be moving to an up-scale life-care facility. The apartments have concrete exterior walls, and I usually listen to small baroque and jazz trios at moderate sound level, But I think headphones may be the way to go when I want to crank it up for large orchestrations like Aida or Mahler's 2nd.
I've been impressed with the sound of my cousin's Sennheiser 800S with his McIntosh headphone amp. I have an Ayer QX-5 Twenty with a headphone driver that Ayer tells me is very good. I suppose the answer is to try the Ayer before buying the McIntosh. I've downsized my rack of Ayer gear to a KEF LS60, but I really like the sound of Ayre electronics. Advice sought.