I have been playing with WHS for a while now, and while not perfect, I think it is pretty usable. However, there are a few areas where I think it could be made a little better...
I think the biggest issue is with the initial configuration for the first user. I ran mine off of the share (which if done right, could be the better/preferred solution as there would be no need for the CD/autorun issues and such...). Here are a few thoughts on a possible way of doing the configuration:
Have a default website that the user could surf to upon first boot. This would ask the user for basic network setup information (with an option to just use the defaults to keep it simple). This would allow the user to see the name, workgroup, ip, etc... How would the user know to go there? Simple, a poster or note taped to the box saying: "Go here to setup your new server" (Kinda like dell or hp send with their new printers/computers...).
Next, They could then click next (where the server would add the new configuration) and then it would offer to set up user accounts. After the user accounts are set up, it could offer to install the connector software pre-configured to use the users that where just set up. Then it would be good to go...
One other thought, there needs to be a way to make the shares a bit more visible on the client computer. While they are on the desktop, that can get lost in the mix (especially with as many icons as some users have on there desktop...) and yes, there is the right click on the connector icon, but I still have a hard time getting users to right click anything... (Besides, that's not the most intuitive solution...)