I would be one of the guys who pines for the "good old days." I promised I'd never be this way, but it happened a few months ago when I said in a meeting, "I wish every one of you punks could do a real "show" with turntables, carts, editing phone calls on a reel to reel." It's true though. While its great to be off on holidays and weekends because of computer automation, there is a reason it was called the "good old days."
None the less, after starting out in full-time 30 years ago this summer, I'm still at it. Back in the late '80s while working in Atlanta I made the decision that major market was not for me anymore. I had stops in my home town of Phoenix, Denver, San Diego and Tucson before Atlanta. I moved up the road to Cleveland, TN (near Chattanooga) back in 1994. I was making about the least I'd made in my radio life. Almost 15 years later I am still doing what I love and I'm making a very comfortable living for the area. I've never regretted my market "downsizing."
All that to say I think the days of market jumping are well over. If you invest years in a market and make yourself very visible in it, it can still be an enjoyable and semi-profitable living. God knows it beats roofing.
Hey, Beave...I had a gig like that in Phoenix working on a pea-shooter country FM. Rent was traded out, meals, gas, etc. Salary was 19K but I was living like a king. A local watering hole even gave us jocks free drinks to come hang out at his place. It was great fun.