3. E-Mail Management Is Weak
Though the iPhone's 2.0 OS update added bulk e-mail management, it's not very good. You can tap individual messages to mark them for deletion or movement to another folder, but there's no "Select All" option for deleting or moving batches of mail at one time. It's also not possible to run a search term and delete the results, so forget about easily wiping correspondence with particular people.
Ideally: Apple could make bulk e-mail management more robust simply by adding the features described above.
The workaround: There's no truly satisfying alternative. Accessing your e-mail account via your provider's Web-based interface is the only option for more control. It may not be as pretty as the built-in iPhone mail app, but you'll get some of your functionality back.
2. Remote Wipe Costs $99 Per Year
The iPhone was definitely in your pocket when you got into the taxi, but now that you're home, it's nowhere to be found. What to do? If you aren't already paying $99 per year for MobileMe, you've got no way to nuke your phone from afar and protect personal information.
Ideally: Apple could offer a pay-per-use remote wipe feature, without requiring a MobileMe subscription. That'd make it less like buying insurance and more like canceling a lost check.
The workaround: A $2 app called iSecurity (Find My Phone) creates a spoof app called either iPasswords or iBlackBook. The app pretends to hold your personal information. Each time a foolish criminal tries to enter the password for this app, it e-mails you the phone's location. As an alternative, consider securing your iPhone the old-fashioned way with password protection.
1. AT&T Is the Carrier
As iPhone users outside the United States begin to enjoy tethering and multimedia messaging services (MMS), AT&T's exclusive hold on the iPhone angers existing customers and may be irritating Cupertino as well. The cellular provider is slow to provide tethering and MMS, and it'll likely charge a hefty sum once it gets around to adding them. Add long service contracts, higher data rates, and unfair usage conditions, such as the inability to use SlingPlayer over 3G even while other AT&T phones can, and you've got plenty of good reasons to hate your wireless carrier.
Ideally: AT&T's exclusive deal with Apple could come to an end, by contract or by Congressional action, and Apple would take its business elsewhere, namely to Verizon. That, or AT&T would stop treating iPhone users like second-class customers.
The workaround: I haven't tested this, but visiting a site called BenM.at and following instructions detailed at iPhoneHacks will reportedly allow tethering without having to jailbreak your iPhone. (Disclaimer: There's always a chance that AT&T will punish you for being sneaky.) If you're just fed up with AT&T's service and want to stick it to the man, unlock your iPhone and switch to T-Mobile--the only other major U.S. carrier using the iPhone-friendly GSM radio band--until a better offer comes around.