Thank you all for all the constructive feedback. I really appreciate it, and it let me think about some of the aspects that I had initially missed.
As much as I love being the early adopter and a big Apple fan, the Pebble still fits my usage requirements very well. I really can't justify $350 for glamor and fringe usage scenarios (for my daily use, at least). Some cool features that would be neat, but I really don't need them for now. I was trying to rationalize that it's not much money -- I do make a 6-figure income, but I still try to live frugally for early retirement -- so the price tag still didn't sit right with me. And I think it'd make my wife and daughter happier if I got more mileage out of their present, instead of ditching it less than 6 months into ownership.
I considered the possibility of just trying it out for 14 days, but that just seems like abuse of resources to me, and rubs my sense of ethics the wrong way a bit. Well, I'm now more aware of what it can/can't do thanks to everyone's input, so I think I'll just wait it out for the next generation, or if the Pebble ever dies. Thanks again, everyone.