If you get unlucky, you might get ORD 145 out of training at Envoy. Reserve there is currently around 8 months. If you want to transfer to DFW 145, the reserve there is over a year. Only way to break guarantee is to pick up OT, which means commuting to a job with 8 days off. Don't do it. Just don't.

Commuting to an average regional when you have a reasonable hometown regional (Skywest) would be borderline insane.