I'm in the same boat. Wasn't blown away by AW1, thought for sure the AW2 would be an improved design, better battery life, more features, so I was waiting for AW2 to be released. I'm not impressed at all with AW2 either, same size, same battery life. The improvements are nice, but to me AW2 just means AW3 will really be the first actual 'new' AW2, which I definitely plan on buying. Since I know I'm gonna upgrade next year, now I'm consider getting a used AW1 off craigslist for $200 (or less). It will give me a year to try it out and see if it's really worth the money for me, and in the mean time I will likely be able to recoup 75% or more of my cost when I resell, as opposed to a new Series 1 or Series 2. I'm really banking on all the reports that watchOS 3 makes AW1 much more useable.
Any one see a mistake in my thinking here?
I have heard of problems with craigslist apple watches not being properly unpaired which makes them expensive paperweights. Just be sure you can pair it to your iphone. I think the better route is to get a new one from Best buy on a closeout sale so then you get return rights and a full years warranty.