Have you considered that your ears may be too clean? Seriously, I had bad ear infections every 2 months on average and had many diving plans destroyed because of it. Then when it happened again in Egypt I saw a specialist doctor and he saw the problem within 3 seconds: I kept my ears too clean. Her recommended using a drop of some special olive oil in both ears every day and stop after a month. I found it really funny but had nothing to lose. And since 2013 haven't had a single ear infection because of it.
Now you don't have a problem with inner ear infections but by removing too much of your natural protection layer may be too vulnerable, just in a different way.
lol, too clean? Just to be clear, it's not an ear infection thing at all. It's because the skin just outside of my eargina tends to be very sensitive, and prolonged contact with anything makes it feel raw and sore.
Have you ever tried Azla Xelastec Eartips @warrenpchi ?
Nope, but again, not a fit issue at all.