This is the primary design flaw with the iPad. This tablet can't be the normal person's computer unless every normal person has a tech friend/relative to keep the tablet working/updated. So while Woz is correct that the tablet will be the normal person's computer, Apple's iPad is not yet that tablet.
What iPad user can't figure out how to use iTunes to sync the thing? My 65-year old mother figured out how to sync her iPod classic. How is iPad syncing any different or more complicated than what people have been doing for a decade? iPad does not require a tech genius - or 12 year old kid - to keep it working.