Yes, I did my time...saw alot of changes, too.
Started at a small Ohio station at the tail end of 1988, had no experience except that I knew alot of music and was always interested in audio. I'm still amazed I got hired, but it was a small-town station. Not power wise though -- the FM was 100,000 watts, the AM a "daytimer", signed off at sunset, different times throughout the year.
When I started, the FM was elavator music, the AM sort of adult contemporary. FM ran off four big 10.5 inch reel machines controlled by some archaic automation system. You should have seen the board...no sliders, just bigass knobs and a couple VUs.
I worked the AM in the mid-day, recording the farm report on an Otari 5050 and reading the noon news in addition to playing 45s on two awesome Technics turntables (installed in custom cabinets including a plywood box filled with sand -- you could pound your hand down as hard as possible right next to table and no effect whatsoever!).
Later, I worked through alot of transitions -- we went CD automation, "Classic Rock" when that genre was just beginning. I went from recording on carts to hard drive. Lots of cool stuff...
Got out of the biz around '98 or so. Now a geologist.