Being someone who does a fair amount of outdoor activity (cycling and hiking mostly), and knowing a few people who are crazy about their Fitbits, I ended up looking into some fitness tracker-oriented smartwatches, landing on the Garmin Vivoactive HR with it's HR monitor and built in GPS. It's a very attractive device for $250, especially if fitness tracking and mapping your workout is important to you.
$250 is maybe the upper limit of what I'd want to spend on a smartwatch, but the Garmin has been great for me as a simple intuitive device that knows what it is good at and doesn't try to complicate itself.
Though you can cram a surprising amount of information and interactivity in these devices, it goes against good sustainable user experience to make a wrist-top computer as robust as a smartphone. Smartwatches should be a bundle of sensors and quick intuitive bits of display information, not a surrogate to my smartphone.