My biggest problem with SkyDrive is that it doesn't work with network shares.
I'm running Hyper-V R2 on my server box and it's responsible for providing shares for my network of server VMs and workstations. I can't install SkyDrive on any workstation or server VMs to do the synchronization with the cloud, because the SkyDrive client application can't handle UNC paths or even network shares mapped to a drive letter. So the only place I could install the SkyDrive client is on my Hyper-V server. The problem is that Hyper-V doesn't even have a real UI to run something like SkyDrive. Everything in Hyper-V server is managed through the command line.
SharePoint Workspaces have the same limitation. It's almost as if Microsoft is dissuading people from saving anything at all to a local server. They want everything to be shared via the cloud. If I were inclined to put on the tinfoil hat, it wouldn't be difficult for me to believe that Microsoft is going to eventually kill Windows Server in favor of Windows Azure.