In SH3 the visibility is just 16-18000 metres when using the 16 k environment mod (And only <9000 metres without it), so you must consider the 50 km figure that OLC said more as a real life matter than something usable in the game.
If you plot the target using the IWO and make an average after say, 6-10 estimates, you should have a fair degree of accurancy and be able to do a good end around at full speed plotting a paralell course in the limit of visibility, i.e. a course parallel at 15000 metres to the target/convoy (in good visibility), so you never lose the sight of the tips of the masts, or at least the smoke plumes.
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One day I will return to sea ...
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