Battery life and charging options: Charging your smartwatch is a hassle and the biggest downside to trading in your manually-wound or button battery-powered watch. A Fitbit Versa might last 3 - 4 days between charges, but a smartwatch like the Samsung Gear Sport or Apple Watch will need recharging every couple of days and sometimes every night if you are tapping on the screen regularly and using its apps.
Finding and installing apps is another sore point. Android Wear 2.0 has two ways of installing apps: On the watch directly, which is woefully awkward, or through the Play Store on the Web, which is okay. Watch faces for Wear OS exist in the kind of state Android phone apps were in during their earliest days—all over the place, so good luck searching. Watch makers would do well to include some sensible, category-spanning offerings by default in their devices.
For deeper integration with your Android phone, you can give Google's Wear OS platform a try with Fossil's $275 Q Control touchscreen smartwatch. It lacks GPS and support for NFC payments, which is why the Gear Sport is a better fitness-focused smartwatch for Android users, but Fossil's Google Assistant integration and stylish design make it a solid contender. However, smartwatches with Qualcomm's new Snapdragon Wear 3100 processor start shipping in October, so you may want to hold off until we put them to the test.