I voted "buy" though I'm usually a wait person. I originally got the Stainless Steel at launch, had it for a week, then returned it because I was honestly a little ashamed to have spent $800 (SS and classic leather), which is more than the cost of my iPad, for something that was cool but not vital and felt so first-gen.
But then this past February, I started thinking about the watch again and how cool it would be to have and how ok I'd be with the Sport pricing. The issue was I did not like the aluminum or Space Gray finishes for a watch. But the combination of the release of the gold aluminum plus Best Buy knocking a hundred bucks off the price (plus an extra $50 off an open box one) made it worth it to me to jump in. Picked up the gold Sport and the brown Classic leather band and I love it. If I'd waited for Gen 2, I'd probably be sweating the pricing again, but I spent so little on mine (including gift cards, I probably spent a total of $250 for watch AND band) that I'm happy to have it.
It's a cool device, very cool, but it really isn't a necessity like the phone is or even as fundamentally useful like the iPad. If you do lots of walking, running, etc, I can see it being even more useful (I don't exercise enough) but the reminders to get up and move around are having an effect on me for the better. The notifications are the best. Being able to pause/rewind podcasts while driving from my wrist instead of reaching for the phone is arguably a safety benefit. So since we're probably in mid-latish cycle, with the deals going on, you don't have much to lose by trying it out for the 6-8 months before a Gen 2 could conceivably come out. If Gen 2 is incredible, I can sell my gen 1. If it's just a small bump, I can wait for gen 3.