I present the reader with a progression of Apple PDA and Apple phone comments from Newton to iPhone. It’s interesting how far in advance this one was called. The train of thought is surprisingly simple: Jobs believes people don’t want handwriting recognition, they want keyboards. What did he kill? The Newton, based on handwriting recognition (or a bulky external keyboard, or an eMate that should have run Mac OS instead). What did he get development started on? A handheld with a smart keyboard built-in. That’s it. That’s the major difference. Well, that and third parties being able to develop for it, the little fucker.

1997

Instead of working on the handheld Newton, Jobs thinks that Apple should be developing stripped-down “network computers” that could be used by “mere mortals” as alternatives to PCs in accessing information and software from the Internet.
San Jose Mercury News as quoted by “David Farber”:http://www.interesting-people.org/archives/interesting-people/199705/msg00039.html

1998

“Apple makes computers, and computers have keyboards”
Steve Jobs quoted by David MacNeill

2001

“You can’t imagine how many people think we’re crazy for not doing a Palm,” said Jobs, “I won’t lie; we thought about it a lot. But I started asking myself, how useful are they, really? How many people at a given meeting show up with one? I don’t think early cultures had organisers, but I do know they had music.”
Geek.com quoting Fortune

2002

Steve Jobs speaks [in the Financial Analyst Meeting call] about how they decided about 3 years ago, they felt that PDAs would eventually evolve into next generation Cell Phones, and that PDA’s will become a smaller market.
“MacRumors”:http://www.macrumors.com/2002/07/20/no-apple-pda/

2003

“I get a lot of pressure to do a PDA. What people really seem to want to do with these is get the data out . We believe cell phones are going to carry this information. We didn’t think we’d do well in the cell phone business. What we’ve done instead is we’ve written what we think is some of the best software in the world to start syncing information between devices. We believe that mode is what cell phones need to get to. We chose to do the iPod instead of a PDA.”
Steve Jobs at D, “MacObserver”:http://www.macobserver.com/article/2003/06/05.9.shtml

2004

Jobs stated that he is proud not only of the products Apple has shipped, but also the products Apple has decided not to ship. When asked to elaborate, Jobs replied, “an Apple PDA.”
“AppleInsider”:http://www.appleinsider.com/articles/04/06/07/jobs_apple_developed_but_did_not_ship_apple_pda.html

During a Q&A session, one individual pleaded with Jobs (as he clenched his Treo), begging for Apple to produce a PDA/Phone hybrid. Jobs told the audience member it would be best to remain happy with his Treo.
“AppleInsider”:http://www.appleinsider.com/articles/04/06/07/jobs_apple_developed_but_did_not_ship_apple_pda.html

We got enormous pressure to do a PDA and we looked at it and we said, “Wait a minute, 90% of the people that use these things just want to get information out of them, they don’t necessarily want to put information into them on a regular basis and cellphones are going to do that.” So getting into the PDA market means getting into the cellphone market. And you know, we’re not so good at selling to the enterprise where you’ve got, in the Fortune 500, five hundred orifices called CIOs. In the cellphone market you’ve got five. And so we figured we’re not going to be very good at that.
Steve Jobs at D during an interview with Walt Mossberg; as quoted by “Niall Kennedy”:http://www.niallkennedy.com/blog/archives/2004/06/walt_mossberg_i.html

So the problems encountered along the way that Jobs tried to solve were:

• People wanted to mostly get data from the device, not put data in.

• PDAs and cell phones appeared to be merging.

First, iSync put the user’s contacts and calendars on the iPod. That was popular, but not perfect, and people actually started to clamor more for the Apple PDA at that point, now that a concession had been made. People may read that information more than they write it, but they still wanted to write it, especially mobile.

So then Apple starts the work on a PDA but sees that cell phones are the way to go and that they don’t want to do a cell phone (at the time). PDA shelved. But, then, something changed and now Apple wants to do a cell phone and then spends three years (it’s been said, I presume PDA time was included) working on the concept only for the slick stuff in Leopard to make them move forward on it (which is what the iPhone is running if the Safari user-agent lines on Mac Geekery).

That’s a bit of a crazy path, IMO.