Slightly more technical than Surveyor, but not actually hard to learn. I got to grips with it after a couple of afternoons. The gotchas for me were first of all spending ages working out how to specify UK National grid, which I finally found under the view menu after a quick RTFM, and then having to re-install the terrain textures with hardware compression turned off, again after a bit of RTFM. In TRS2004 and 6 the map on the terrain is a bit crude, but once you go up to TS2010 and specify the 5m grid it is an excellent aid to laying out rough tracks, roads and rivers.
Since I am modelling historical routes from the 1910-1930 period Google earth images are less useful to me than the ability to lay on old OS map down on the terrain. What is more useful is knowledge of how to clean up and sharpen scanned images of the maps, but even without that, I would still say Transdem shouldn't be too hard to learn for anybody willing to research the national mapping system for the area they want to model.
I tried to use the built-in route editor in Transdem to lay out tracks, but in fact I found I got much better results by bringing up the mini-map in surveyor, then using it to position the start and end of track, road or river splines by right-clicking on the mini-map to get close to the ideal point, then crossing over into Surveyor to make any position adjustments before the final left-click.
As has already been said, the hard part is working the gradients to get cuttings and embankments in the right places.