Just looked at the plant details submission page again and I saw what you were talking about for 'Will Naturalize.' To me that seems like a very ambiguous term as well. Wouldn't it be regionally specific as to where a plant will naturalize? Or if it simply means that it is possible for the plant to reseed/naturally propagate (as in not a sterile hybrid), wouldn't 'Sterile' be a more accurate description?
FWIW, naturalization vs invasiveness to me is a difference of whether a plant is a native that will propagate instead of an introduced species that aggressively chokes out native species (or more simply, included on some authority's list).
I know Rob already acknowledged the limitations of that current method, but it may be worth bringing up in the overall conversation if changes are being proposed.