Fast guys helping the slow guys will ALWAYS bring resentment.
I recall racing against two sailors way up in the National rankings. After finishing between the two in the first race I proceded to sail over and point out to the one we had beaten that tacking on the shifts was advantageous. It was like he was looking through me and not hearing my "advice". As we were only close to the eventual winner only once in four races and my targeted slow guy close to us only once, I only wanted some competition. In looking back on my early days of racing I took the fake it till you make it route. The only thing we knew were a few rules, and didn't know how to make our boat go fast in all conditions. I was too proud to admit to anyone that I had no clue what all these terms meant, just nodded in agreement and thanked them. But that is my story, and we are different.
In some respects racing is like golf, you can screw yourself by making knee jerk decisions and will either learn from them, or it will frustrate you to the point of building resentment.
The person or persons who want to organize, lead and maintain a fleet or club need to be like a sports coach in that it is more than your knowledge, it is how you impart the information to each "player" and who needs the coddeling or the swift kick in the butt. IMO. Excellent thread!