How to re-create the structure/functionality of a customized menu from Word 2000 in Word 2010

My office is migrating from Word 2000 to Word 2010 (2013/365 is not an option - our tech folks don't support them).

I'm a legal secretary, and I've built up a rather large collection of various merge documents (60+ at last count) that I use constantly to file things with the local court.

In Word 2000, I have these all accessible from a single menu button in a customized toolbar: it opens a menu with individual items and sub-menus of other items grouped by relevance (orders/objections/withdrawals/letters, etc) into the sub-menus.

I *think* I've got a pretty good idea of how to replicate the *rest* of my custom toolbar into 2010's quick-access (I think that's what it's called?) toolbar, but I haven't yet found anything to point me to how I can re-create the document menu system itself.

Each item in the menu is basically a hyperlink to the relevant document.

Since I often have to add/remove/change documents as the relevant laws and Court rules change, this is a VERY dynamic, easy-to-use, and handy system that has to be easy to change as needed, i.e., it can't be a static creation that I'd have to re-build from scratch every time there's a change to a menu item.

The structure (very simplified) is like this:

My Docs [menu button that accesses everything]
     title of sub-menu1  -->  opens sub-menu1 items
     title of sub-menu2  -->  opens sub-menu2 items
     various links to constantly-used items I don't want in a sub-menu
and so forth.

Each sub-menu cascades off of the higher-level menu.

This is the heart and soul of 15 years worth of work (most all of it in Word 2000) that allows me to be incredibly fast and efficient in getting literally hundreds of documents processed and filed with Court each week.

Unfortunately, The Powers That Be don't see the wisdom in simply doing the smart thing and going with a 3rd-party app that restores the menu/toolbar functionality that was killed off in Office 2007 (they're about as technically-minded as a piece of moldy toast).

Fortunately, the migration isn't set to happen until March or April.  That being said, my machine is coming in a couple of weeks, so I'll have time to play around with 2010 to see if I can get everything in working order ("he said optimistically").  I'm just thankful that 2010 has more user-customization than 2007, though I've read a number of highly disparaging commentaries about the 2010 hype being greater than the reality!

For what it's worth, I've got a similar situation with Excel (2000 --> 2010), but that's a LOT less stuff to worry about:  only a handful of macros and a MUCH smaller menu to re-create.

I'd appreciate any advice/assistance you folks can provide.  I'd even tape a chicken bone or rabbit's foot to the new machine if it'd help - this is looking rather daunting!

Thanks!!