
Apple
AirPod Pro Series
Apple-integrated, great ANC but can cause ear pain.

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Same here. Transparency mode for when I could be near traffic, livestock, dogs etc. Noise cancelling for the rest of the time
I really like my Powerbeats Pro 2, they sounds great and fit well with the Apple ecosystem. I use them over the AirPods Pro 1
I used to think like that too, totally with the idea of the small case small form factor for everyday use but the powerbears hit different, the first couple of days when i got the first powerbeats it wasn't fun to fiddle with the hook but then it became a second nature i don't even think about it and i got it for the gym nothing more because the buds that i had back then were falling out of my ears everytime. The second i got used to it i started using it daily not giving a shit about the case size cause they eere that good and loud, then i got the fit pro it was the same thing fiddle with the hook get used to it but now the ANC is an extra plus on top of all the good things about the powerbeats just the noise level is a bit quieter. Now the powerbeats 2is a different story i love it, it's almost the same thing as the powerbeats one but has ANC I don't really care about the heart rate monitor i have my watch to do that. I. Short the powerbeats 2 is in my opinion the best out of all of them eventho i hate the look of it but who cares once you put them on. You have to try it for couple of days to get used to it.
Since mukhang willing ka naman na dalawa yung gamit mo: 1. Powerbeats Pro 2 for the gym - solid na rin ANC neto if maingay sa gym mo, or if you simply don't want being bothered 2. Shokz Opendots One - open ear para safe ka sa long runs If budget won't allow, just go for PB2 tapos disable nalang ANC when doing long runs
I would definitely go with the Powerbeats Pro 2 https://amzn.to/3HUwPxp
Based on what you said about integration, sound quality, and qol. I definitely think they are better than airpods.
Dre best pros gen 2 do a really good job, but the safest option is bone conductive headsets. Edit: the name was actually Beats Powerbeats Pro 2
Beats Powerbeats Pro 2. They have little hooks to keep them on your ears and they stay in even on rough gravel roads.

Apple
AirPod Pro Series
Apple-integrated, great ANC but can cause ear pain.

OnePlus
Buds 4
Budget king, great ANC/sound, but no wireless charging.

Anker Soundcore
Sport X20
Secure fit for sport, durable, but connectivity issues.

EarFun
Air Pro 4
Budget value, good ANC/sound, but cheap case, noisy transparency.

Beats (Apple)
Fit Pro
Workout king, secure fit, but wing-tips tear easily.

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Denon - PerL Pro

Ranked #1
Beats (Apple) - Fit Pro

Ranked #1
Sony - WF-1000XM5

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Shokz - OpenFit Series