This screenshot of Freespire shows how many levels in you have to go to get to OpenOffice. Do the people that build these structures ever actually use them? The answer is probably no! (consider how easy it is to launch things from the command line...)
Windows's "Start Menu" is a pet peeve of mine...with the amount of stuff I install, it either fills between half and all of my 1280x1024 screen, or it takes forever to scroll to the desired folder. This is why I love Xfce's Menu (and, to a lesser extent, GNOME's menu): you can get to the programs one submenu in. And, of course, all of the applications are in neat little categories, so that I don't have to look to see where the hell on the menu the "Inkscape" folder is (not that I'm trying to insult Inkscape – it was the first cross-platform app that I use that came to mind).