Hearing loss varies a lot, and can be problematic in a number of ways. I suffered a fairly large hearing loss because of jet engine and machinery noise in the Navy, and that's on top of a genetic problem. Most noise induced loss does start with high frequencies and work it's way down, because of the way your ears are built. The type of loss that runs in my family is broad band, affecting all frequencies more or less equally. The Navy stuff gave me a ten or fifteen year head start on the sort of loss my brother and father experienced, with maybe an added fillip in the high treble. It's a drag.
Often enough frequencies in the upper octave of our hearing tend to be irritating. For a person with 'normal' acuity, with a cut off around 20,000 Hz, that means that tones above 10,000 Hz will tend to be unpleasant. As your upper cut off goes down in pitch you can well find that the highs become harder to take. I suspect that's the key to Wade's friend's love of brass bridge pins. The added mass cuts down the response of the guitar across the board, but primarily in the higher frequencies. It may also suppress certain things in the mid-range that Wade notices more than his friend does. Sometimes what the guitar 'sounds like' and what it actually does can be pretty different. It's one of the 'joys' of trying to figure this stuff out.
I've made several guitars with side ports over the years. Feedback from customers, and measurements I've made, suggest that one use of that feature may well be to improve the experience for folks with hearing loss. From what I can tell the port acts like a 'monitor', directing higher frequency sound toward the player, and it gets more effective as you go up in pitch. With a high-end loss that could be helpful.
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