1999 Can we sell this Tablet? NO
2002 Can we sell this Tablet? NO
2004 Can we sell this Tablet? NO
2006 Can we sell this Tablet? NO
2008 Can we sell this Tablet? NO
2010 Can we sell this Tablet? YES
2000: Can we sell this tablet (or phone)? - NO, because hardware isn't good enough and even if it were, why would anybody buy this, if they can't watch movies or listen to their music without too much hassle? Let's build a music (& movie) store, so that when the hardware is ready, we are ready too.
2005: Can we sell this tablet (or phone)? - No, the hardware is good enough now, but we need great software too. Let's build a great mobile OS (from scratch) and leave the legacy behind. And give the 3rd party developers the SDK and tools to build great apps for our device.
2010: Can we sell this tablet? - YES, the software is great now, just like hardware. Order 15M iPads to Foxconn and ship the damn thing!
I don't believe for a second that Jobs had the iPad in mind in 2000.
They probably just brainstorm, try different stuff internally, see what works and see if they can make a product out of it that meets their high expectations. Jobs was no doubt an important part of this process but it is not impossible for the culture and process to outlive the person who helped create them.
I would not be surprised if Jobs was speaking honestly when he talked down tablets in 2008.
No, he was lying ;)
Watch his D8 talk (With Walt Mosberg), it's available in iTunes (Podcasts -> Apple Podcasts). He (Jobs) says that they began working on a multitouch tablet in the early 2000's, but around 2005 decided first ship a phone (When I saw the rubber band thing, I said: My God, we can make a phone out of it!). When that got successful, he put the tablet off the shelf and the rest is history.
Again, watch the D8 talk. It's awesome.
Bill Gates certainly had something like it in mind in 2000. I have an example of such a device in my living room. (tc1100 - Mine dates from 2001) The "raw" functionality (for a technically savvy person like me) far exceeds the typical use of the iPad. It even has the same screen resolution. Still, I don't do anything on the iPad that I didn't do on the tc1100, and do everything on the iPad -- the whole gestalt is just more pleasurable to use.