Nicely presented, Chris.
Skip the simplicity in my mind at all times is who is in control and if not how can I get into control. Being clear ahead in the situation you describe is not enough. Even if your sails fill seconds before a collision is possible, you lose the protest and the heat.
If a windward boat is getting tactical to hold you off like at the port mark of the finsh line, you will have to suck it up and loose a position in the finish.
Thinking ahead in such a port tack I will gain control by slowing slightly to tack behind the windward boat and take my chances of beating her at the next tack. The longer I wait to do this the less likely I will finish ahead of her.
Remember to in the situation that 18.3 allows you to call for tacking room for an obstruction.
...94