I was using the Pebble Steel since it's initial launch and I picked up the Gears S2 Classic when it launched.
Things I have learned:
1. Long battery life of the Pebble watches is overrated. I'm ending each day with the S2 with 40% battery and I'm totally fine with that. Could stretch it to two dasy if I wanted by turning off "always on" mode. The reason I'm fine with one solid day of life? The charger. It's just so simple and convenient.
2. The e-paper screen of Pebble is overrated. I really expected outdoor readability of the S2 to be a problem. It's not. The S2 screen looks great indoors and out. And since it has a built in ambient light sensor I never have to mess with screen brightness or turn a backlight on to read it indoors.
3. The Pebble app Store is awesome. I really miss it. The Gear S2 app store is really bad right now. Especially if you don't have a Galaxy phone. Can only access the paid apps if you have a Galaxy phone. If you want an S2, better make sure the stock apps are gonna meet your needs.
4. I have found fitness tracking to be much better on the S2. I don't do anything intensive, but for my daily walks it gives me much more information, feedback, and alerts than I ever had on Pebble. I find it to be more accurate than Pebble, but I have seen others complaining about the accuracy of the S2.
5. S2 needs persistent apps capability. On the Pebble if you open your music player app it stays open. I can walk and change tracks or adjust the volume without even looking at the watch. No such luck on the S2. Most apps are force closed and you typically find yourself back at the watchface anytime you check the watch. I believe the original Gear 2 had the option for persistent apps, so hopefully they'll add the option in future update for the S2.