Interesting device. I'd no idea they existed.

I'd guess those first hearing aids, in that they were from an audiologist, had custom ear fitting (audiologist pours a substance in the ear, which hardens into a soft silicone-like tip for the aid).

If not, I'd suggest that. I haven't had this done for hearing aids but have for ear protectors (same process as for in-ear monitors on-stage musicians use). I can wear those all day (even quiet motorcycles subject riders to damaging levels of wind noise at highway speed — never mind on the track).

Short of doing that, I’ve had good luck with Comply ear tips to make in-ear phones more comfortable. They probably have models for airpods and Bose eqip't.

My wife, before becoming an ESL teacher was a sign language interpreter for the deaf. She taught me a technique for communicating with my grandmother who was quite hard of hearing: get them looking at your face (maybe by touching a shoulder if they're faced away. Wait a moment for them to face you. Enunciate. We're all using lip reading to some extent.

Aaaand more out of left field: I've seen at least one clinical trial of a short course of rapamycin being used to reduce age-related hearing loss. I'd made the assumption that, if it was a rapa, it must be something to do with inhibiting M-ToR. The writer I mentioned that to (Gunnar De Winter) pointed out that it could be any of a number of other things going on...