From my experience, the satnav uses the waypoints to calculate the route, and will take you on any road that will get you as close as possible to the waypoint - usually measured at a rightangle to the road, if the waypoint is not actually on a road.
Since it is going off road, it takes no account of obstructions, as long as it is as close as possible 'as the crow flies'. If the crow chooses to fly across a railway line, it will do, possibly leaving you actually some distance away as you try to negotiate the obstruction.
Note also, that waypoints on motorways pose their own problems. If the motorway is new, the waypoint has resolve to the correct carriageway, otherwise you end up travelling up and down each side of the same road.