Hi Nina,
I may be a little too used to the newer tools, but I find IIS7 much easer to configure than IIS6. I have installed DNN on Vista many times and it seems nearly automatic to me but I am used to using newer versions of all necessary tools. If Vista/Win2008 II7 is hard to come by, than this could still be done using XP/Win2003 IIS6.
I realize that the poster is new to DNN but if he knows how to set up ASP.NET apps, setting up DNN especially one that is already configured should not be too difficult.
The reason I suggested to do all of this on a staging server (localhost/test) is to make sure all the modules that the site currently employs are going to work in newer versions of DNN. I have heard differering opinions about whether or not to keep up with DNN upgrades but I fall into the category of people that believe you need to keep current if at all possible.
While a site may work fine in 3.3.7, there are many new features to enjoy with new realeses; performance upgrades, simplified administration, fewer postbacks, better menus, easier to make compliant, stronger security and the list goes on. If this site is made with fairly standard modules, the whole package may upgrade without a hitch and if it does, you would have a whole new world of apps available to you.
Setting up a staging server and successfully setting up an old version of DNN would be an inaluable learning experience. In my pre-DNN days, I had a bitch of time setting up ASP.NET sites. Now I can set them up in minutes and I have several staging sites running on my various computers and this makes my production servers nearly invulnerable. If he has time to read DNN books, setting up a staging server and going through the upgrade process will be a very enjoyable educational experience. You do not need to be a developer, I can barely write a line of code but I have made many great DNN sites.
Mike