My main concern is if they have sales on the second generation this holiday season.
It would suck to get one and then barely 10 weeks later have them going for around $100 off.
I'm not planning on buying at launch for that reason. There will be at least $50 off at certain places, and Walmart of Bestbuy might offer $100 gift cards or what not. Either way it's only 1-2 months and you could save a decent amount, so I'm certainty waiting.
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Why do you want update to steel?
If the sport model was not matte, I think less people would consider upgrading to the steel.
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Why do so many people want a new design and seem to be so fixed on that? Imo the watch design is classy and not something we laugh about in a couple of years. Think for example about swatch watches - same design for decades, still rocks though.
The design is fine for what it is, and is not particularly bad looking at all (despite my dislike for square shaped watches, the rounded corners adds to a pleasant balanced look, with enough class). While the watch does not look partially chunky in person, if you can imagine what the next iteration of the design would be - you can see why people are waiting for the redesign.
They will not likely change the design, but rather further evolve it - it'll still likely be square with rounded corners, but likely to become even more tapered with much smaller bezels, and potentially much slimmer. It's going to be much more handsome imo.
If they don't go that route, then they will probably also produce a round model as an alternative.