Generally you're right in that's kind of a strange attitude to have. But when it comes to brand new products, it's not necessarily a bad idea. The first iPhone was kind of cool when it first debuted, but really didn't hit its stride until the 3G model and the app store. Unless you're the type to buy every iteration of a device, then waiting around for the 1st revision isn't a bad idea.
True about the original iPhone but I enjoyed it just the same -- came from an arguably better featured Treo too. No regrets at all and that sucker was $499 too. I didn't upgrade again until the 3GS arrived, again no regrets thanks to iPhone OS 2.0.
If I like the Apple Watch once all the details are revealed I'm buying and will enjoy I'm sure. People's adverse position on Gen 1 is overwrought. Even mature products have design faults because they are in effect all- new or changed enough from the previous model.