1. The Cost
For those cost-conscious CIOs who love a good deal (meaning: deep discounts for bulk purchases), that’s not going to happen with the iPhone. AT&T is not offering any kind of discount on the device. On Tuesday, Apple and AT&T announced announced that charge-by-the month plans start at $59.99 (for 450 minutes) and run up to $99.99 (for 1,350).

A recent IDC survey found that just 10 percent of users researching their next cell phone purchase were OK with paying the full price for the iPhone and inking a two-year contract with AT&T.

In addition, many analysts and pundits have pointed out that there may be plenty of bugs and problems with iPhone 1.0, and that could turn many people off. "I am the quintessential early adopter, and I’m not doing it anymore," says Richard LeVine, a security and risk expert for mobile devices at Accenture. LeVine says he bought a Suzuki Sidekick when it first came out, but adds, "I’m not buying a first-gen V1 iPhone." He’s a huge Apple fan (he bought a first-generation iPod), but with the iPhone, "I expect firmware and patch releases and bug fixes." So he’s going to wait on the iPhone. In addition, he claims like many others that he doesn’t like iPhone’s touch screen because he "wants a phone with physical buttons."

2. Apple’s Never Been Enterprise-Driven
The BlackBerry’s turf is mobile corporate users. RIM has more than 8 million CrackBerry fanatics right now, and that’s going to be tough to crack. Even more difficult for Apple is the fact that RIM recently delivered new devices with more multimedia capabilities—the Curve and the Pearl—that work just like other "corporatized" BlackBerrys.

Apple-related products (Macs) are usually just too different and too expensive for most companies. The iPhone runs the Mac OS, and according to a report on the iPhone from Jack Gold, founder and principal analyst at researcher J. Gold Associates, "this is a major constraint, since few third-party application vendors (for example, Good Technologies for a push e-mail client) run on the Mac."