I honestly think it will be how they did the first one. They will announce the Watch with the iPhone but it will launch Apirl. But I could very well be wrong. I love the Watch but I really hope they wait until Apirl to release a new one. The Watch is expensive for yearly upgrades in my opinion.
If you have any doubts about liking your watch return it within the 14 days. It is not for everyone but the only way to know is to test it our yourself. No one really know when the new AW2 will arrive.
It will have been two years in September since they debuted it. The AW was released 6 months after they first debuted it (as was the case with the original iPhone and iPad).
To answer your question, nobody knows. We only have speculations/rumors.