Interesting discussion. How each generation choses to remember an individual or an event reflects as much about that generation as it does about history. Sometimes, as in the example of Washington and the cherry tree, the "history" is made up, but that's not the point. The point was to use GW as the personification of honesty and integrity; virtues that it was felt should be passed on to the next generation.
In the 1950's, Daniel Boone and Davy Crockett personified the ideals of courage, freedom, democracy, and masculinity; values and virtues that reflected the WWII generation. The historians of the 6os and 70s also looked to contemporary events and such things as the Equal Rights Amendment, civil rights, and Native American protests, etc. to look at history from a non-white, non-male perspective. Their interpretations of Boone and Crocket were not so glowing.
The same thing seems to be happening today, not just with how we interpret the symbolism of Confederate monuments, but also with how we consider historical personages: Jackson (both Andrew and Stonewall),Lee, Forrest, Lincoln (was he gay?), Jefferson, Wilson, the list goes on. The pitfall is, of course, that neither the interpretations of the 50s nor the interpretations of today provide a complete portrayal of the person or event. The issue that I think we are all grappling with is not only how we want succeeding generations to remember the Boones and Crockett's, but what is the lesson we want them to learn from Boone and Crockett?