I love coffeecup software but I think for this you will want to consider utilizing custom client side scripting like javascript (this could get very messy and some users have set their browsers to not display), or server side logic (much neater and stable).
If coding or scripting doesn't sound like your thing. It might be possible to have one menu with the main options and then several pages with tables for comparing options.
Alternatively, if you are on a very tight budget and have lots of time you can create a dynamic menu with links (DHTML menu builder, or the Flash menu builder) and then a new page for each option with new dynamic menus for each additional set of options. I really don't recommend this because it would not be fun when the time comes to make any changes.
I'm a Microsoft fan so if I were doing this I'd use asp .net, AJAX, and C#.

However, everyone has an opinion and lots of the world will disagree with me on that.
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