The windward-leeward format is not the best place to try racing for the first time. Going downwind with the chute up, you
have to worry about people coming upwind etc. This did not happen much in the days of triangles. The racing scene I remember from the late 70s/80s was more social, more recreational than it is now. I suggest that this young fellow consider doing some of the distance races on Lake Ontario, in particular, the short-handed series. The starts are more relaxed, you get to race on all points of sail, and the atmosphere is much closer to what I recall from my youth. There is a PCYC-Youngstown race coming up I believe. I encourage this young guy to give it another try. I think his experience will be completely different.