I wouldn't get back in for a full time job.

Scale back your finance job and find a Part 135 freight operator that you can fly 1-3 days per week for.

You will get the best of both worlds in this situation. You get the stability, 8-5 schedule, 4-5 weeks vacation and with the 135 freight operator you get that needed break from the monotony of crunching numbers/ dealing with people.

In the Regionals you are probably going to spend most days flying next to a 25 year old. Some people can handle this just fine, but a lot of people will have problems.