Wi-Fi printing. More and more printers are wireless, and when you're on the road, it would be great to be able to print your notes, contacts, map, or whatever to one of them.
Other issues that affect everyone
There are a few other things I'm not sure are enterprise-specific but are annoyances nonetheless. So here goes:
First, my iPod Touch often is slower in switching among apps than it used to be now that I have the 2.0 software installed; a few times I thought the iPhone crashed after waiting 10 or more seconds for something to happen. I've heard others with similar problems, all those who upgraded pre-3G devices. I also have occasional e-mail access glitches, which tend to occur after I move from one Wi-Fi hot spot to another (but only sometimes): The e-mail doesn't read new messages, and instead seems stuck in a "Connecting" loop. I have to power down the iPod Touch and restart it; then the e-mail loads fine -- until the next time. The 2.1 software update didn't fix this, and I can't tell yet if the 2.2 update has finally stabilized the device. Stay tuned.
Second, syncing apps when you have multiple computers is tricky. Some third-party apps disappear when you sync on the second computer, and reappear when you later sync on the first. Others never disappear. Yes, I disabled the sync function on the second computer's iTunes, but it mysteriously re-enables itself, so I often forget to disable it again. There's a similar issue with music synching: My home Mac has my iTunes library, but when I sync at work, iTunes wants to replace my iPod Touch's music. So I have to turn on manual music syncing so a sync at work doesn't delete my music. Devices like an iPhone and iPod Touch are going to combine personal and business use, and are highly likely to be synchronized across multiple computers. Apple needs to let you designate the master computer for each type of information (and for each account), so it knows what to leave alone when syncing to a "guest" computer. And it needs to understand that the computer that "owbns" my music is not the same one that "owns" my e-mail.
Third, Apple no longer includes a dock with the iPhone, and its expansion connector has changed, so not all previous peripherals fit. Bad Apple! That type of incompatibility is just not necessary, especially when some of these Bluetooth chargers come with $100-plus earpieces.
Fourth, if you're going to put a camera in a smartphone, why wouldn't you support the sending of those pictures over the cellular network via MMS? The iPhone does not.
Fifth, can't Apple and Adobe figure out a way to support Flash on the iPhone? Flash files can be resource hogs, and badly implemented ones can cause crashes (ask any Firefox user), but these are so prevalent on the Web and so much a part of rich Internet content that it's nuts not to support them in a device as rich-Internet-focused as the iPhone. Ditto with Java support.
Finally, I wish the iPhone could store passwords, so when I go to a hot spot, for example, I wouldn't have to re-enter all that information each time. While I'm fairly proficient with the touch keyboard, it's still a pain to expand the Web page to be able to find the fields I need to complete to log in.
(For those of you wondering why I don't have an original or 3G iPhone: As much as I would like an iPhone 3G, I'm not willing to shell out nearly $1,000 per year for the service, which is what it would cost for me to shift from my current cell carrier, whose family plan I'm enmeshed in and can't get out of because other family members live in areas where AT&T's coverage sucks. So an iPhone would be a wholly new, additional plan. Fortunately, I've discovered that since I'm not a road warrior, I am perfectly happy having a regular cell phone in one pocket and the Wi-Fi-capable iPod Touch in another. Most of the time, anyhow.)
This story was updated on Nov. 21, 2008, to include the changes made in the iPhone 2.2 software update.