Agreeing a 100%, we need a set of improuved tools to draw the intended track, to add time, speed, DR and observed fixes, and so on.
Why the pencil can only draw a cross? why not a circled cross, half a circle, and some other marks? Is it a difficult task?
A sextant on the bridge (and at scope station) not only to get a star altitude; also to measure an horizontal angle on the land.
A mark from UZO or the scope at Capt. requirement as stated in
http://www.subsim.com/radioroom/showthread.php?t=156347.
and so on.
The SH2 capability to get the lat-Long coordinates of a point (or to mark a point given the lat-Long coordinates) and the great circle path from a departure point to an arriving point.
And an easy mode to draw landmarks (mountain peaks, lihthouses, and so on) on the maps.
For the attack plot, we already have
http://www.subsim.com/radioroom/showthread.php?t=158098