This is babbly and a bit dry, so feel free to skip it.
So apparently there was recently an OS update (navcore 7) that blew away from old options, including the multi-stop trip planner. You can get this option back by using the old style custom menus, but that blows away options for the new "help me" and "map correction" features. While the first one I don't ever expect to use, the second I think is exciting to have community updated maps and I want to encourage using this feature. Let me be clear. All these features are on the device, so there just aren't menu items for all of them all at the same time (there is also this cool "show me where the GPS satlites are near me" thing that also goes away in v7.) So you can't get there from here on a navigation device feels very silly.
What is cool is the device mounts like a USB media storage device, so I can go frob things under linux. I think the device itself runs linux and there seems to be an existing community who is on top of this whole menu thing and are pining for a SDK for v7.
You can also down load dennis hoppers voice to give you directions, but that costs money.
People also report that TomTom's customer service sucks.
Oh and so far I'm liking my new toy.