He needs to do what is best in the long run for him and his family and take the one year upgrade at CPZ. This is a very rare opportunity and he'll be a senior lineholder within months and if he wants to bypass upgrade for a while and 'pretend' he went to SKW then he can simply do that. Why not have the opportunity to upgrade? Who knows, CPZ might have a base in ORD someday anyway. Even if not, I think the seniority progression will cancel out the negatives of commuting. Upgrade is already just about to come down to ~14 months. People starting in the next 2-3 months will upgrade in 12 months if they want to.

Why on earth go to SKYW when this is available, with the class date right in front of him to boot?

The path to a major airline is not the right seat at a fee-for-departure airline for half a decade while a major hiring spree is ramping up. The family needs to understand this. There could very well be a million extra dollars made because of it; you never know with how the timing and periods of stagnation go in this industry.

He needs PIC time now, more than a single guy with no family does.