Let me try to stop laughing long enough to answer that question.
OK, I think I’m OK now. Here goes.
One, Microsoft does a horrible job of marketing its apps. It may have the greatest set of apps on earth, but it can’t even figure out what to call them, much less how to effectively communicate to people what they do and why they are awesome. Seriously, I am a long time Microsoft user and TechNet subscriber, and I don’t even know what Live Mesh (what a stupid, stupid name) is. I think it’s the (God knows how many times) renamed FolderShare app that Microsoft bought back in 2005. I actually used FolderShare before it became a casualty to Microsoft’s (lack of a) marketing plan.
Two, Microsoft’s non-core apps tend to be very kludgy. Dropbox may only be a folder on my computer, but it’s a folder that I can access with a click of an icon, and easily drag items into. Sharing is as easy as a right click. As far as I know, there is no way to mount Sky Drive as a folder on my computer, in the absence of Gladinet or some third party work-around. Even when Microsoft adds features that compare favorably with other offerings, like the ability to sync multiple folders and more space, it generally trips over itself in some way- like the fact that you can’t access Sky Drive via Live Mesh. Or the fact that you need two separate apps in the first place. Between the ever-changing (and ridiculous) names and the (real or perceived) learning curve, many people will choose the ease of Dropbox.
Which is sort of too bad, because the battle for the cloud is wide open.
I agree with Ed Bott that the latest Dropbox security breach is a big deal. I’m a believer in the cloud, but every day I see more and more evidence that the cloud is still being formed, and no one has adequate security in place. I also agree that scale matters in the cloud. I would trust Amazon or Microsoft to keep my data safer than Dropbox. But I’m not willing to spend hours trying to figure out how to mesh (pun intended) Microsoft’s products into a workable solution. And if I feel that way as a tech blogger and geek, how do you think the typical internet user feels?
The fact is that you install Dropbox and you’re done. To replicate that with Microsoft either is or seems like (it really doesn’t matter which) the equivalent of a 1000 piece jigsaw puzzle. It might be beautiful, but few people have the time and patience to tackle it.
I have no doubt that for someone like Ed or Paul, who are very learned in tech in general and Microsoft in particular, the Windows mesh/mess of apps, when placed in the right order, is a fine, and maybe even preferable, solution.
Meanwhile, the rest of us go on living our lives, using Dropbox and hoping that Dropbox gets its security ducks in a row, so we don’t have to go try to figure out what Microsoft’s apps are called that day, and how they work.