I used to use Sennheiser RS-130s. The ones I had, the headphone stands were also a charging stand.
If you know where his hearing is bad maybe some sort of equalizer to boost those frequencies. That made more of a difference to understanding speech than just playing everything more loudly.
Also, there's a hysteresis effect to how loudness affects one's hearing. You'll need it louder and louder if the ears aren't given rest time (never let rock musicians control the volume

).