I ended up getting some PowerBeats 3's from the local Apple Store
They work, they may not be the best in the world, but the W1's pairing capability is excellent
I bought some PowerBeats 3s specifically to wear with my AppleWatch 2 while running, and I've been pretty disappointed, specifically because of how poor the pairing "magic" is. Sound quality is fine, comfort is good, battery life is ridiculous, I don't care about brand, and cost is quite frankly not a concern to me. I chose them entirely based on what I thought would be least hassle pairing with the W1 chip.
Where it fails so hard is its inability to recognize that I want to play music from the watch to the headphones. It literally takes minutes, not seconds, but MINUTES, every time, to start up my music prior to starting my run.
First, and this isn't the fault of the PowerBeats, when starting the music app on the watch, you have to force-touch and manually change the source to the watch. Every. Damn. Time. This takes a few seconds. Then you turn on the PowerBeats, specifically while not yet in your ear because it's impossible to distinguish the on-chime from the off-chime so you need to watch for its light to come on. And that seems to take 3-4 seconds for some reason. Not instant. Assuming you still have your playlist already selected, you press play. Now, you have to wait through a full timeout cycle where the watch will inform you it can't find the headphones. I think this takes close to a minute. This also happens every single time you first initiate playback. You then have to cancel out back to the playlist and click play again. A few second later, it'll finally send sound to the headphones and you can start your run. But don't accidentally pass through any wifi locations your watch knows the password to or it'll automatically halt playback. Thankfully in this case you just have to go back into the music app and press play again (it won't hassle you about not finding the headphones), but that's still disruptive when you're in the workout app and trying to run.
That said, they work awesome with the phone. And that's actually the problem. The headphones always want to be paired with and receive music from the phone. All that headache I spelled out above applies only when the phone is in range of the watch, or the watch is otherwise on a wifi network it knows. If you wait to start your music until you and your watch are out of range of the phone and wifi, it actually performs like you'd want. And if the stupid watch app would just remember that you prefer to play music from the watch, not the phone, it would truly be magic. (it still defaults to phone even when it knows for fact it can't find the phone, forcing you to force-touch and switch to watch source).
I also have an iPad Air on the same iCloud account. I've never managed to get the iPad to play to the PowerBeats, but I've never tried with the phone completely out of range. Hand-off type features do work between my iPhone and iPad, iMessages are shared, etc, so they're definitely sync'd up in that regard. The PowerBeats are supposed to work with the iPad in this scenario. But they don't. The iPad can see them; I can switch output to them manually like you can with AirPlay, but it will timeout and say it can't connect to them. Always.
I say all this because the experience has completely changed my mind on buying the AirPods (which I'd have loved to have at my desk for teleconferencing). The W1 chip is not magic, aside from battery life.