Photos by Ryan Octosa (2022)
Well, long story short, I ended up returning the AirPods Pro and I got a pair of Beats Studio Buds instead, which fit my ears a lot better.
How's the Setup Process Like?
The setup process for Beats Studio Buds I went through was pretty much the same as the AirPods Pro, which isn't a surprise considering all Beats products are now part of Apple (Beats was acquired by Apple in 2014 for USD 3 billion.)
All you need to do is to open up the case with your iPhone nearby, and a prompt will appear for you to connect it. The process is pretty intuitive, really. No need for an external app either.

If you are an Android user, fear not! Both AirPods Pro and Beats Studio Buds are also compatible with Android phones.
Love Colors Other than White?
Unlike the AirPods Pro which comes in white only, the Beats Studio Buds is available in 6 different colors:
How Does Active Noise Cancellation Compare?
Per my memory, the noise cancellation feature is more powerful on the AirPods Pro, but Beats Studio Buds still has it pretty decent overall.

Specifications
Here's a quick comparison between the Beats Studio Pro and the two generations of AirPods Pro. AirPods Pro is built with a little more pizzazz overall, but if it hurts your ears, Beats Studio Buds is worth considering.
FEATURES | |||
Listening Time on Battery | |||
Water and Sweat Resistant | |||
Active Noise Cancellation | |||
Transparency Mode |
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Touch Gestures | |||
Ear Tips | |||
Dynamic Head Tracking** (more info on this below) |
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How It Looks |
* Both Transparency and Adaptive Transparency modes allow you to listen to outside sounds without having to remove the earbuds, but Adaptive Transparency will actively reduce noises above 85 dB.
** Dynamic Head Tracking is a feature that tracks your head movement to deliver an all-around-you (surround sound) audio experience, making listening a more immersive experience.
Over and Out
If AirPods Pro didn't hurt my ears in the first place, I would've kept using it and I wouldn't have found out about Beats Studio Buds the way I did.
The device I purchased and returned was the 1st generation AirPods Pro, but considering the 2nd generation one is practically identical in shape to the 1st generation one, I would likely have the same problem.
The 2nd generation one however, has a pair of extra-small ear tips that I did not try because it wasn't available in the 1st generation one. I wonder what the chances are that my ears would like it, considering they didn't like the other 3 tip sizes.
The ear tips that I've been using in my Beats Studio Buds are very likely medium in size. I remember trying out the other ear tips inside the packaging but I recall switching them back to the default ear tips that were pre-installed on the ear buds when I bought them.

Your Turn
Did AirPods Pro hurt your ears as well? What did you end up doing?