Help Getting My AS Dad Wireless Ear Buds

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I am trying to get my father wireless ear buds and he is being impossible.
Now I have AS, and I am pretty sure my dad does, although he is in denial, just as a disclosure.

I don't know the anatomy of his ear, but I've tried pro beats, apple air pods, jaybirds, and he vetches about them all falling out of his left ear (ugh).

So I wanted to know if you have any you may recommend or better, what store (I am outside Washington DC) I can go to and get some expert help fitting him? Think of like trying to get a kid special clothes, obviously ordering by the internet is not going to work. Thanks.

What's the amount that you're able to afford to spend on them?