I own the first generation 2016 model.
- Small pill shape means I can carry it around with me everywhere.
- No tangled wires.
- iCloud integration.
- Easy switching between devices.
I don't mind the battery life, though some people seem to have problems with it.
The Apple headsets have always fit me fine. They don't come out when I'm running on the treadmill, or on the elliptical.
I sometimes only get one headset to connect.