Depending on which phone and which plan the iPhone costs between $2000 and
$3000 $6000 over two years.
I just switched providers and the three phones I got for the Wife, the Mother-in-Law, and myself and the service for those phones should run me on the low side of the iPhone range in the same time period.
Besides that, I really don't need my phone to do much more than make calls, send texts, and take pictures. By those criteria, I am pretty happy with my Synch (and it's even more phone than I need).
So, yeah. Up to now, I've been saying "I'll wait until the third generation of the iPhone." Unless my needs drastically change between now and then, however, I doubt I'd get one then either.