CAG 19,
Yours is an excellent question! But one that IMHO can only be answered by each individual wargamer -- or, more specifically, each "Gamemaster type who builds most of the stuff for everyone else to play on" -- by him or herself. Needless to say, whatever you choose to do, that's the right way at your place!
For myself at my place, I am a bit of a psycho obsessive-compulsive perfectionist type when it comes to terrain, and I have settled on a compromise with regard to the somewhat profound "paths or no paths?" question, which comes into play a great deal in the NWF and Afghanistan
I make a point to provide at least one path capable of supporting figures moving between contours -- HOWEVER, depending on the size and scale of the game being played, it is not always necessary to actually USE THAT PATH in order to move between contours.
If I'm laying out hills for a small, more "skirmish"-y feel game, I will likely tell the players that their troops can only advance up or down the hillsides/mountainsides via the visible stepped pathway provided -- but if I'm setting up a big refight of the 1879 Second Afghan War battle of Charasiab, with multiple battalions of Brits & Indians assaulting a dug in Afghan regular army supported by tons of tribesmen in the high hills South of Kabul, I will allow troops to advance up or down contours from anywhere, so long as they spend the required movement penalty for going through "Rough Terrain."
This means a bit more tedious labor for me when I build my hills, but in the long run, for me, it's worth it.
Here's a pic of one of my 2-contour rocky frontier hills, with some 72nd Highlanders poised along the stepped path leading from the first contour to the second
Here's one with some tribesmen poised on the rocky steps between the base of a smaller hill and the top of its contour