Dave Donaldson read my whiny post about the friction I’ve got with TFS and working offline. Dave details his solution to the issue on his blog, and as always with Dave, it’s a smart way to get work done.
One additional step you should take to make working offline smoother, particularly if you’re a fan of working in small iterations: Set up an offline repository so you can keep your small changes checked in and maintain a working system as you go.
(Note that with TortoiseSVN you don’t need the full Subversion installation to get a working repository going. Just use TortoiseSVN’s “Create Repository Here” context menu option to set up a repository in an empty folder.)