These answers are not terribly helpful. Though keep in mind many regionals are do not have a unionized SOC and as such do not have to have a set or published payscale.
That said, it depends on the regional. Skywest, Expressjet and the other larger carriers will probably top out higher and make a career seem reasonable for a few, but not for all. Assuming you get into a supervisory role you can probably top out in the $25-30/hr range at a larger regional, at a smaller regional or one that is built to fold in 10 years or less you're looking more at $20-25. When I worked at the late Colgan Air they had a 10 year payscale that topped at $20/hr for DX, pretty abysmal.
After 5 years? Probably somewhere around $18? Regional pay isn't pretty because they do not want you to stay long term. Benefits will also be pretty bad, think a 1% 401k match and healthcare coverage that is severely lacking.
Maybe if you loved the city and had a spouse who made a decent living, but as a single person or as someone who is the primary income earner in the house it's not really feasible outside of maybe two or three carriers.