AH ... yes, my wife I gave for a present one year AirPods Pro, works well for her, same reasons, many hurt her ears. The Samsung Buds Live sound like a similar concept.I hear that wife has tiny "earholes" so even the smallest tip doesnt fit well (painful)
I gave her my never used pair of "samsung buds live" and shes on her 2nd set of those.. they dont go in that far.
I have tried about 5-6 but they either dont work as single buds or have odd issues.. the regular buds2 are my current set and about ready for a new set.
I wish I had more options. I am tempted to try the BEATS FIT PRO. Years back, same issue with the standard "new" beats at the time before the pros called the Studio Buds. The Pro now have some small "wings" on them.
I also back then tried the Power Beats Pro because they have ear hooks. They came close in fit but once again, my left ear would loosen up after a while and lose sound quality.
I loved the Studio Buds at the time but returned because of the fit. I loved the Power Beats Pro's too and even using them on phone conversations was awesome, but again, the fit for the price I was paying just didnt quite cut it.
Im tempted to try the Beats Fit Pro and even the Power Beats Pro again, so turned off by the Bose issue.
I also have over the ear Bose QC 45 that I still have to unpack and I better do that soon as I think they maybe still under warranty.
Bottom line, its been a long time now but I if I had to put everything I tried together and comment about sound and quality feel I think I would say I like the Beats products the most. (trust me, I was never a beats fan before this) Next for comfort would be Bose for sure. now if they just didnt fail all the time from what I read. The Bose app is terrible too, jack of all trades.