Have you thought about the ear gear covers. They are supposedly good at keeping sweat of of HAs and some models have a clip on them that can be attached to clothing so you wouldn’t have to worry about losing them.
I use them to prevent static electricity from my long hair turning off my aids. I don’t cycle so I don’t have personal experiance with them in that situation.
I’m in Toronto and I ride with the Mississauga Bicycle Racing Club. When I started two years ago, they had to push me up some of the hills. Now I graduated to the fast group and I don’t get drop. My club’s fast group has a bad reputation of being too much of a hammer ride all the time. It took so long and a lot of suffering to get to a level that I can keep up with them. I was never athletic in gym at school. I’m not sure if I could keep up with you guys in Boston though.
I am thinking of getting a cheaper bike for racing later if I stay in racing.
I signed up for the Mt. Washington Hill Climb this year, not too far from Boston. I drove up Mt. Washington two years ago and it was scarier going up then coming down! I just want to make it up in a half decent time.
The Giro Nine’s not bad; it’s cut above the ears and the ear pads on the straps are not uncomfortable. As a cyclist, I like it because it’s made much like a cycling helmet. I’ve got one of the early ones; the new ones are a little different-- YMMV.