I used wireless jaybirds before they were known. It was still when I was in Japan so maybe 6 years ago.
My first were Sony MW600s in about 2011, used BT earbuds ever since. I loved them so much I bought a second pair, as for a long time BT earbuds seemed universally flakey and unreliable judging by reviews, and the MW600s worked flawlessly.
I mentioned Jaybirds because they seem to be the ones everyone knows. Not a fan personally, had some X2's, the remote glitched out after 13 months due to, presumably, sweat. Pressing pause sometimes initiated a call and I'd have to cancel the call quickly. Jaybird quoted me about £50 to repair them, plus had to arrange my own shipping to the states. Nope. Last of their products I'll buy.
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hadn't heard anywhere in reviews about your #1. Very interesting in the case of fit and the fact that they are cheaper at costco, I love that place! Even at $250 (plus the 2% points and the money back that costco gives you at the end of the year so more like 240) I would rather have all Apple products on the things I use every day. I have found, as I dive deeper and deeper into the apple ecosystem, that if everything you use is apple things tend to run seamlessly across the board. So with that said, at $150 they are the same i paid for my powerbeats wireless I bought for a headless headset for work, and I can use them seamlessly across my mac, iPhone, iPad, watch and while not seamless you can very easily use on the ATV4. I ended up leaving the job but had the powerbeats wireless 16 days when I tried to bring them back (they work and sound great for music and for people on the other end I'm told). So I have a feeling my powerbeats wireless will collect dust come monday even more than they already do unless I can find someone to buy them lol.
I'd strongly advise you don't buy the Bragi Dash until you've read loads of reviews and feedback from users. I followed their development very closely and a LOT of people had problems with losing connection and all sorts of of problems.
There's a reason the latest Bragi's eschew a lot of the features of their first product - they simplified it to make it work better. I remember reading endless complaints on Reddit about how (fairly frequent) firmware updates would alternately make the Dash better/worse from people using same firmware. I honestly suggest you avoid them like the plague.