I almost read it a different way.
The "one in tens of millions" could go either direction; there's a chance that he knows something almost everyone else doesn't, and sees what the Mentors Three see--
A blank canvas with limitless potential.
Rather than "Jobless" meaning "weakest class incapable of being called a Job", it could be interpreted as "falling outside the Jobs system, fully unbound and unrestrained". And if I'm honest, that's
precisely what Cross has become.
If anyone could see the 'other side' of Cross' situation, it would be the Hero himself.
Him saying it's "regrettable" is still something I can't square with that idea as of now, but it would depend on whether there's some precedent for another "jobless" in the annals of history, and what became of
them.
Could be that Cross's "Jobless" title could make him incompatible with the Heroic bloodline, somehow, or something. So it's not "regrettable" because he sees Cross as not worthy of Elysia, but because the closeness between them is going to run up against something that he believes they can't overcome.
**actually, I'll tack on what
@zeinzki made note of. Even if her
dad has no issue with the Jobless thing, there's a reality that Cross is still largely looked down upon by everyone, entirely because of that title. And going alongside the Hero, would be politically and socially problematic (like hugely so).
And I think that's a very big part of it, in this case, or at least a facet that's easily identifiable without making guessing about the larger untold lore of the setting.