........ On more than one occasion I've waited for the harbor to be 90* abeam to tack only to find I could not steer to the point I wanted, requiring additional tacks.
Don't feel too bad about that. Even after decades of sailing I regularly missed the optimum tacking point, especially when having battled high waves and winds for many hours and finally managing to lay the harbor entrance abeam. Under these conditions, it is easy to become over-eager to tack into the protection of the harbor (only ending up having to choose between getting darn close to the ubiquitous fringing reefs or turning tail).
Altough it may sound pretty straightforward to calculate where to tack, as longs as one knows one's vessel well enough and can make the necessary corrections for set and drift, the reality is often a bit different. Squally conditions, together with the unpredictable currents and waves close to many harbor entrances, have a way of making a mockery of even the most elaborate plots and calculations.....
For that reason, we always used our GPS's COG (course over ground) track , whether from the previous tacks en-route or from a special short test tack, to show us where exactly to make our final tack into the harbor and what to expect once we did.
In highly complex situations, I have always trusted hard-won empirical evidence over soft models and calculations.
Fair winds,
Flying Dutchman