Seriously, as an engineer I doubt it will be easy: the success of this update procedure depends on reliable upgrade of every single component in the system: not just the kernel/drivers/gnome/etc, but things that I installed afterwards, including those that I compiled, including those that depend on kernel version. For instance I have no reason to believe that VMware will continue working. Similarly, I expect to see issues with video drivers.
And finally, my friend who's been running Gutsy beta got an unbootable laptop after a series of online updates. Linux is solid software. However, all software has bugs, especially if it's forcefully put on a 6-months release cycle.
There is a very good reason why you don't see new Debian releases very often.