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I guess my question is do you need a watch? Are you thinking of flipping the watch? If you can wait, you can probably get another deal during November/ black Friday sales but it's not guaranteed and I don't know if it'll be better. If you have the funds, you should get it just to ease your mind because Google is saying they're going to support phones for 7 years... (I don't think so, but who knows).
I hope they make good on the update cycle. But yeah, I would prefer a deal with the watch.
If you're looking for a deal on the watch I think it's a good deal then unless you want the LTE version.
They let you pay the diff and upgrade to the LTE, I believe.