The pros are known to be worse in staying in the ears, wanting to fall out. There are tips on Amazon that you can get that works for $23, not acceptable for $200 earbuds. As far as comfort and hurting the ears over time, the pros do hurt over time, but like you said in 2 weeks it got better.. well our bodies adjust and get used to things. I agree, they hurt if you wear them for ahile. Other then that, the pros are better, but comes at a price of what I listed.
Thank you for sharing your experience. It is interesting you had the opposite experience on how well Pro stays in ear. In my case they do better than all other true wireless buds I used -- buds+ and Jabra sports/65t/75t. Guess it may depend on ear shape.