This is a huge problem with the iPad. And frankly, I believe Apple really screwed up with this issue/process.
Like Steve always says if the user thinks about X then we did Y really wrong!
If the user has to have a PC or Mac to use/setup/maintain/etc the iPad then Apple really screwed up the concept and requirements of the iPad user!
People should be able to just use their iPad. One should be able to setup their iPad without connecting it to a computer. Now if they wish to connect it to a computer and swap/transfer information and files that's great, but it shouldn't be a requirement.
Many people are going to want to just use their iPad. They don't want to have to download stuff to the computer and transfer it over, and Apple is projecting this as the way for people to use their iPad just as they do their iPhone.
I believe Apple should move away from this strategy with future models of the iPhone OS products. I would also like to see a WiFi backup to a remote drive connected to an AEBS or Time Capsule, or even have a USB hard drive available, and backup all information from my iPad and iPhone right there. It should wirelessly backup all changes daily. I am not just talking contacts or scheduling but the entirety of the iPad backing up. Then if my iPad is stolen, or if it breaks, I just connect my new iPad and it wirelessly transfers the whole thing back. Completely eliminate the purpose of a computer connecting to the iPad. One last thing, why doesn't the iPad allow wireless backup to a Mac? Why do I have to physically connect the damn thing every time? It is a major flaw in the whole point of an iPad...
I suspect with iPhone OS 4 things will get better, but I want to eliminate the NEED to have my Mac to connect to my iPad. If I want to swap the information over from my contacts or schedule, I should just setup a connection on the iPad and it should always do it wirelessly without connecting the iPad to computer. I know MobileMe does this, but the point is the iPad should never have to be connected to the computer for anything especially for something as simple as turning the iPad on the first time or managing contacts and scheduling.