I'd go for Wordpress without hesitation. It's easier to understand for users, and there are multiple plugins available that will let you do quite complex things without programming knowledge. I'm less familiar with Joomla but it's a generally less intuitive user interface IMO.
I think the twentyeleven (default) theme comes with just a single menu set up but a swift Google will let you set up as many as you want, and they're easy enough to configure. Pretty sure the default css goes down to three level menus at least as well. That covers 1 and 2 in your list.
3 is out of the box behaviour.
4 is easy with a plugin, 5 is more complex I think, unless there's a plugin that'll do that as well.