I had a Pebble Time Steel. Loved the thing to death.
The battery was a bit degraded and I got tired of not being able to acknowledge Pagerduty notifications (even though I could receive them), as well as not having any fitness features whatsoever (other than the steps counter). So I bit the bullet and bough an Apple watch.
Within two days, I stop using the Pebble. Yes it's nice, but against what's essentially a supercomputer in my wrist, with a bunch of useful apps... I switched. Sure, having to charge daily is not _ideal_, but I can put it to charge while I'm having dinner or in the shower, and it will be full pretty quickly - specially if you are just topping off daily. It is not as convenient, but I didn't hate it as much as I thought I would.
The screen is always on too. I disabled the feature, didn't see much of a difference.
Just this weekend, I had a pretty spectacular fall from my bike. Fall detection kicked in - I did not need emergency services, but it was a reminder that some features can be life-saving.
My company's SSO supports IOS, which means it is now integrated with my watch. Pretty secure too, the watch will lock if it is removed from my wrist. It can unlock my machine (and my car). I can control other devices. I can take just the watch outside and still receive phone calls, or buy groceries. Many of those things, I couldn't do with the Pebble, or they would be more cumbersome. Yes, physical buttons are nice, but also limiting.
Pebble had the right idea. But they executed too slowly and too late. The fitness focus was missed by them for quite a while, I bet that they could have stayed relevant if they had implemented features like heart rate monitoring.