Yeah.. Google Maps sucks for anything more than a section of routing.. which is a shame.. I love their maping!

 I used Microsoft Streets and Trips to layout the basic route ..  then I hand draw the route to get clean lines (otherwise, you get silly waypoint markers that get in the way). Then I take the image into an image editor to put all the milestone images in.  It's a fairly manual process, and usually ends up taking me 4-5 hrs each year to get this style of map.

But I like the end results.. it's worth it.  

Great map!! No wonder your other tow vehicle gave out - you guys do some miles!!

--kev