Regarding #7...

Sounds like you really want to live in ORD. In the regional world it is risky and unrealistic to plan on a "guaranteed" domicile for any extended time period. If you're just looking at a few years at a regional, OK you might get lucky. But if you're thinking career, the odds aren't good.

Instead, it is safer to select an employer with a significant presence in your desired geographic area...that way you have less chance of getting stuck with a transcon commute if your company closes your base.

SKW is pretty stable, as far regionals go, but RAH has way more eastern flying.

Assume that Midwest will get merged or liquidated, so MKE is not a long-term option.