Pentecost thoughts - the Sailboat Analogy

My wife and I were having a discussion the other night, trying to understand the Gifts of the Holy Spirit in light of the Feast of Pentecost and the relationship of the Gifts to the seven Virtues. The Gifts of the Holy Ghost are wisdom, understanding, counsel, fortitude, knowledge, piety, and fear of the Lord. The discussion came around to how they were related to the Virtues - both Cardinal and Theological – Prudence, Justice, Temperance, Fortitude, Faith, Hope and Charity – since there was definitely some overlap in names and meanings.
I was moved to look up the meaning of a virtue from a recent bible study our parish men's group completed, based on the book Boys To Men: The Transforming Power of Virtue, authored by Tim Gray and my friend, and fellow former Venturan, Curtis Martin. In the introductory chapters, they define a virtue as a "good habitual action of the will" – something we have learned to do reflexively,  so to speak, as a result of exercising the strength of will to do what is right time and again until it becomes a habit (or in the case of the Theological virtues - this "habit" is supernaturally infused by Baptism and strengthened by Confirmation).
This led to reading the analogy of the sailboat in regard to our efforts and God's grace. A Catholic understands that both are needed, as Gray and Martin write:

 "The finest sailboat in the world can't sail far without it's sails. Even with wind and good weather, if the sails are not up, the boat will not make much headway. The sails signify our effort, namely the virtues. Conversely, if the boat has excellent sails, but no wind, it cannot sail. The wind is like God's grace. We can make all the effort and preparation in the world, but without God's grace we will not make much progress in the moral life. Similarly, we can receive the sacraments and pray, but God's grace will not avail much if we do not act. The wind will pass over the ship without much effect because the sails are not up.

This happens to too many Christians. They go to Church and receive the sacraments, but the wind of God's grace passes by them, as they do not put much effort into following Christ. God may be present in our lives but, unless we cooperate with His action, we will not reach our destination of eternal life."

Dom Guéranger, in his commentary on the Feast of Pentecost mentions that there are four major "events" in human history that establish something completely new – The Creation of Man, the Incarnation of Jesus Christ, the Coming of the Holy Spirit at Pentecost, and the fourth has yet to happen; The Second Coming of Christ in Glory, which will "conclude" history as we know it. So it seems fitting that the season after Pentecost should be the longest, as it is the one we are now actually living in, in terms of this demarcation of history. So our challenge is to do the work of maintaining and unfurling our sails and catching the wind of the Holy Ghost as he fills our sails with His marvelous Gifts in this glorious season of Pentecost - essentially the rest of the liturgical year until the Feast of Christ the King in November. (I will note that in the Novus Ordo Missae of 1970 this season After Pentecost is called Ordinary Time)