Training wheels 101 will come later, I guess I'll have to do a whole tutorial on that. For now one suggestion - take the wheel off one side and lean toward it. Auto targeting OFF, map contacts update ON, use the map to check your accuracy.
ID the target, if you can't just use 100 feet since that's an average for large merchants, you can change it as you get closer.
I chopped the range/AOB dial and moved it over so it would fit in the image, worst trouble with SH4 stock is the range on the dial says 11000 yards and hitting the SEND RANGE AND BEARING TO TDC button says it's 9843. As the target gets closer and the masts become more than one pixel wide it becomes easier to see where the actual tops are, but for that distance;
Measures at 9300, my clutzy stadimeter work (squinting at the screen through greasy bifocals) said 9843, 500 yards off at that range is actually pretty good. If the target is moving there will be differences anyway, but the errors should get smaller as he gets closer. Play with manual targeting using map contact updates on for a few months, use the map range checks to twique your techneak.