Right now I don't fully understand where you want to go with this, but I will follow you to see where we end up.
Another way to put the point is to imagine a group of photographers with DX cameras, and an equally skilled group with FX cameras. They set out, each on her own, to make photographs of a range of subjects - portraits, buildings, landscapes, nature, etc - almost like real life. The aim is to have the same framing and perspective on DX as for the corresponding image on FX. Aperture is up to each photographer. Because measurement error is inescapable, they rarely succeed in achieving
exactly the same framing and perspective for the corresponding DX and FX images. Because both groups are equally skilled, the images are equally good, just slightly different. Because the difference in DoF between FX and DX for
identical framing, perspective and aperture is less than the variability of DoF arising from measurement error, some of the DX images have
less DoF than some of the corresponding FX images, some have more, and some have the same.
Of course, if there were a person whose sins were so grievous that their penance was to examine
all the images,
and the photographers were trying hard to achieve the same framing and perspective, the penitent sinner would, over time, see more FX images with shallower DoF than the corresponding DX image than vice versa. How many more will depend on two factors. One is the size of the measurement errors - and as anyone knows who has done anything depending on accurate measurement, whether it is scientific research or carpentry, measurement errors are more common and larger than most people expect.
The other, far more important, factor, is the nature of the images. DX with 16mm at f/8 and FX with 24mm at f/8 both have infinite DoF, and near limits of a couple of meters, so the penitent sinner will see no difference for the landscapes or the buildings. And there will be no discernible difference for full length portraits using a plain backdrop. Or - although here I am straying beyond the narrow issue of equivalence and into the realm of - gasp - photography - for portraits where the photographer
wants the background in focus, as in Annie Liebowitz' brilliant portraits of Queen Elizabeth, where she is referencing the royal portraits by Gainsborough and Thomas Lawrence rather than blindly re-using photographic cliches like shallow DoF. Or where the photographer, noting that the finest royal portrait of the past 150 years (Lucien Freud's 2001 portrait of Queen Elizabeth) is referencing photographic style - it is the size of a photograph and uses a tight,
photographic crop - decides to get a bit closer and/or crop a bit tighter and not have a background at all.