I grabbed the $399 Sport model, and I can afford the most expensive SS model. It wouldn't even put a ding in my bank account. I couldn't justify it to MYSELF. I'm someone who thinks its kinda pointless, but my gadget lust prevents me from looking the other way. Plus I want to see the resell value on these first.
I have a feeling that the used market won't be as good as the one for iPads, iPhones, and Macs. I just can't see someone spending a ton on a second hand Apple Watch. IMHO it's risky to drop a lot of money on a first generation product. I know everyone likes to say, "Look what people said about the iPad, blah, blah, blah!" But this is a different ballgame. It's a $349+ accessory, not a standalone device that can fulfill most of your computing/communication needs.
It won't bomb, but I don't think Smart Watches will become mainstream products. My mother and grandparents own iPads, but they'd never buy a smart watch. The same is true for most of my family, people who love their iPhones, iPads, and Macs. To them it seems redundant. Like, how connected does the average person need to be? Maybe they're just weird ... I'd gladly eat crow if these things really take off.
With all that said -- I can't wait to get mine!