Sam,
Good point, it would be very rare to find enough boats that haven't been upgraded with jib systems, main blocks, EPO's and the like.
I'd suggest the cutoff be no newer than 1983, as that's when the minimum weight was dropped/standardized, even then some older (pre '80) boats are light. It would be hard to arrive at a consensus.
As far as the crew age goes, HCANA rules have master and grand master established.