We're still running ArcGIS 9.3.1 for a short while longer, and have been tiling more of our data, which is great until we have to deploy it. Deploying currently consists of transferring the entirety of the tileset to the production machines, which takes about half of forever, especially on a deadline. We're currently using tar.gz, but would welcome a better approach. Tiling in place is not an option as there is not a "spare" server at the production facility.
Edit: I should mention that the destination server is a long way away, and behind a firewall, meaning that our access to it is limited, and mapping a drive or a share is Right Out. I'd be tempted to use external drives and FedEx, but that would require a physical person at the destination, which tends not to be the case for months at a time.