Turbine PIC/Check Airmen/Chief Pilot
Honestly in the next 3-5yrs or maybe sooner depending on how quickly the airlines ramp up hiring your time is sufficient. Going back to the regionals as a SIC is not going to make you stand out anymore then what you have for a resume.
They want to see pilots who have responsibility within their companies. If you are just a line pilot, then your a line pilot. There are thousands of those. I think that if your someone that has 4k+ with a good amount of TPIC experience you will be just fine.
You wont be the first but you probably wont be the last one either. You just dont want to be down the list to far because as any professional pilot knows there will be a down turn or a merger that messes up our QOL.
And wondering if the grass is greener just remember something new always turns into a grind.