Hey Jonathan! I have a gunmetal pebble Time Steel. I like timeline, the speed of the OS, and in some ways the customizability of the watch faces. At its best, the pebble is a very nice, customizable digital watch.
I also do not like this customizability sometimes. Most of the watchfaces are pretty ugly, tbh. And the apps often have horrid UIs. The pebble desperately needed a heart rate monitor so it frustrates me that there isn't one on my time, but obviously the new series has one so at least they fixed that oversight. Probably most importantly, the iOS integration leaves a lot to be desired. Yes, this has a lot to do with the nature of iOS, blah, blah, blah but a bad experience is still a bad experience. For one, I wanted to track bike rides with my pebble. What I found annoying was that I couldn't start the tracking from the watch. I had to start it from the phone and only then could I control it from the watch. Notifications can be annoying when you can't reply to them.... and nothing beats th speed and ease of Scribble on the Apple Watch. Speaking of notifications, the always on screen means that your notifications are displayed for the world to see if you are, say, on a crowded bus or subway and catch reach to dismiss... something to consider. I also hate the low res screen. E-ink is cool in some ways and it's low power makes it an attractive option for a smart watch but it looks like garbage with analog watch faces especially.
Is the newest version worth it? Not really. I think the Pebble Time 2 with the larger screen is the closest to worth it. I'm interested to see what they do with the extra screen real estate in the future and it's a nice looking watch for the most part. For an android phone owner, I would highly recommend it. But it's not that much cheaper than an Apple Watch series 1 and the integration with iOS just makes the experince so much better.