I actually think the situation is a little bit more nuanced.

In light and medium winds Gavin on the F18 will win more often then loose against himself on the H16,; that is with the current single number measurement based handicap.

In strong and very strong winds Gavin on the H16 will win at least as often or more often then loose against himself on the F18, again with the current handicap ratings.

This is mostly because of the "need" to rate performances that can change from condition to condition into a single number. Often this means that there is a cross over point somewhere, at some wind speed and seastate combo.

We can make the measurement rating systems almost as accurate as we want, but only if we are all willing to put in the effort to measure more specs of each boat, get measured for checks at events and put enough pressure on the organisors to accept the new system.

Like I said, when push comes to shoove we can even train an artificial neural network on the carefully gethered and labelled race data and use that.

Wouter