Gordon's Notes: iPhone: my demands:My working hypothesis has been that Apple hates me, but maybe I'm taking this a bit personally. Another theory is that the Apple has decided this stuff all has to migrate to the net and they've decided to speed up the process by eliminating all alternatives.
... Tasks at least comparable to the 1994 PalmPilot tasks.
Synchronization with Outlook at least comparable to the modern Palm OS (in other words, flawed, but useable). A 256 character limit on contact comments is not acceptable...
A third explanation occurred to me, and a bit of research supports it. Scott Mace, who has an appropriately despairing blog about calendar sharing and synchronization, mentions that the iPhone's calendar synchronization with Outlook is very weak. That's a clue.
Outlook is a the 8,000 pound Mastodon in the world of calendars, tasks, and contacts. It's the immovable object, and it's not simple to synchronize with. Outlook has a very complex and kludgy way of implementing these core concepts, and Microsoft leveraged that complexity to destroy Palm. Apple may have a few Palm veterans in Cupertino, people who are warning them about what it means to try to manage tasks, appointments, and contacts on Microsoft's turf.
Most iPhones will sync with XP and Vista machines, and eventually with Outlook 2007. If Apple wants this to work half-decently (meaning better than Palm), then the iPhone has to approach contacts, tasks, and appointments in a way that's a reasonable match to a subset of Outlook functionality (the most used fields, for example). If the iPhone does this, then OS X must to.
Problem is, Apple has iCal and the (very peculiar) Address Book on OS X, and they're nothing like Outlook. So Apple needs new versions of iCal and the Address book, but that's not going to happen on 10.4. That kind of change can only come with 10.5, perhaps with a new approach to synchronization.
So my latest tortured theory predicts that Apple won't add new PDA/PIM functionality to the iPhone before OS X 10.5 ships (supposedly in October, though I doubt it will be stable before April). If I'm write we'll see something @ Jan 2008.