Ive been playing since beta one. I recently deleted my save and started over. I spawned in LHS 34447. I bought a fuel scoop, and an upgraded frame shift drive, which allowed jumps of a little over 11ly. I then headed first to Aulin, and then to Sorbago. I couldnt plan routes for those distances, so what I did was I went onto the galaxy map, and chose a point that was about half way between Aulin and Sorbago. Then when I reached the halfway mark, I went back into the galaxy map and set a route for Sorbago. I did the same from LHS 3447 to Aulin. All together that was roughly a 250 - 300 ly distance traveled during which time I had to enter the galaxy map only twice. I think factors such as jump drive limitations, and fuel limits probably make route planners quite difficult to implement. I think weve been lucky to get what we got.
Cargo mass is probably also an issue.