Why should I expect any discounts black Friday and beyond? Is that for the IPhone or watch?Tough call. If you wait, you might get a better version, but it's more than a year away (plus you don't know what's in store for sure until then).
Assuming you can swing it, I'd get the newest around Thanksgiving (for a bit of discount), enjoy it, then think about whatever comes out next year.
I see what you mean. Maybe there will be a discount for the phone and watch bought together?I snagged the iPhone 6S Plus for $800 no taxes around Black Friday last year. Regular price was $850 + taxes. So you might get some small discounts around Thanksgiving/Christmas. The new AW might get some discounts as well, but neither is for sure, so up to you if you want to wait.