A post on Dave Winer's blog today reminded me that I've been meaning to write about the big flaw in the iPad. Actually it is a flaw in iOS but I notice it most on the iPad.

First a little background. I've had an iPad for as long as they've been around and eagerly stood in line for the iPad 2's new cameras. More than the first iPad the iPad 2 is a transformative device. It is comfortable to hold in bed to read, it has an amazing cover that just works and it's a bright white color instead of the heavy black. (How the color affects the perception of weight is another topic for another day.)

As awesome as the device is for me. It comes with a horrible flaw. This first came to light the very night I picked it up. After the headache of convincing my credit card issuer that yes it really was me staying in a hotel and buying an iPad at an Apple store I met a friend and we headed out for dinner. Being a Drupalcon dinner there were plenty of tech folks. Since the line for Chicago pizza was longer than the line for the iPad 2 we had plenty of time to talk. Eventually I succumbed to peer pressure and opened the box.

While peeling away the shrink wrap on the box (even the box is slightly smaller than the previous iPad) thoughts of taking a few pictures of the group with the new iPad came to mind. With a creative group of smart people what could we do with this new technology while waiting for a dinner with a week's caloric intake? And then all at once it happened.

Nothing.

Nothing happened that is. Once you press the power button on a fancy new iPad you get treated to the worst part of the whole device. A simple graphic telling the user to plug this device into iTunes before you can use it. Yup the most touted transportable technology of the last year is totally worthless until you plug it into a computer and tell it what it's name will be. All the engineering prowess of Apple can't seem to come up with a way to let you simply type that information in.

Of course once you plug it in your troubles aren't over. No that's just the start of your woes. Next up you have to sync it to an iTunes library. The problem here is that the iTunes library I travel with isn't the one that syncs my iPad. Having been a fan of all kinds of music and film for years I have an iTunes library that hovers around the 700GB mark. Simply too large to fit on a laptop. Now the Apple apologists in the crowd will explain there are ways to sync just parts of it to my laptop and so on. And that's where things get really bad. Could I do that? Sure I could. But the issue is I shouldn't have to.

There is no good reason I should carry the documents, music, video etc. that I want on my iPad around on my laptop as well. Part of the whole appeal of traveling with only 320GB of (very fast) storage is that I don't want to duplicate content. The iPad content lives on the iPad and the laptop content lives on the laptop. I don't need a copy of the latest Ken Burns documentary on the laptop when I just want to watch it on the iPad.

A quick diversion before I get to what I was able to do to get a semi-functional iPad 2 before I left town. Last December I got a fancy new Macbook Air. Without a doubt the best netbook around but that too is another story. When I got it I opened it up in the office, typed in my user name, downloaded a couple of apps and within a couple of hours my key applications and data were all populated from the cloud. If this can work so smoothly for a full laptop it certainly can be done for an iPad. This is a business process problem not a technical one.

So having had my fill of Chicago pizza I landed back in the hotel room. Of course being a hotel the internet was pretty abysmal but at least sometimes you could get on. (Another diversion here to note that no hotel ever understands what will happen when you have a group of uber-connected people like a Drupalcon come stay). While I don't use my laptop to sync my iPad it can still be hooked up. The key is to hook it up and choose "Transfer Purchases". If that's not done you'll end up with a hap-hazard collection of apps being installed.

With the purchases from the old iPad transferred to iTunes it was then possible to plug in my new iPad and get all the apps to sync. With a few trips to settings to re-enter passwords and re-configure the necessary bits this at least got a functional iPad running. It wasn't everything one could want since it lacked music, videos, photos etc. But it works.

A couple days later at home I set about doing the real sync. The key step here too is to make sure you run "Transfer Purchases" since otherwise this causes problems with the restoring of a backup. The process also uncovers the other stinky part of iOS. When you do a major upgrade the whole thing gets backed up, upgraded and then restored. There is no option to upgrade in place. As a result the process of setting up two new iPads and upgrading two iPhones to iOS 4.3 took the better part of a full day.

The rumor-mill is alive with talk about a new MobileMe service coming next month. And many of these rumors speculate that it may have something to do with Apple's new death-star-rival of a datacenter coming online. Whatever the new MobileMe looks like let's just hope it helps solve the tethered iOS problem. iPad and iPhone are a pivotal part of my on-the-road and stay-in-touch-with-home life and it would be great to have this annoying 'leash' problem solved once and for all.

Once that's done maybe Apple will make iOS at least work better with a keyboard... but that's another topic for another day.