WKKM in Harrison is a great example of that. Dave Carr would hire fresh grads from Specs to work cheap (but were still good) and wet their feet until they got their foot in the door at a bigger station.
I think that is the same with all markets, radio and TV. In the shop where I work (small market) we usually see good news people step up to large markets, mediocre ones get into public relations, and the ones that can't hack it get into retail.
But you are right, if they are good their either are snarfed away by a bigger station or go looking. In a few cases you still see good talent in small market radio, and that is usually the case where they reached a level of satisfaction with their career, and have settled in to a comfortable position.
I just returned from the U.P. where I spent a whole week on the Little Manistique drowning worms, and renting beers with my my wife, son, bro-in-law, and his family.
There were some expected dogs in the radio pack, but some real winners (IMHO). Here's an overview...
On a trip to Munising, 1400 was dead carrier all day.

Their FM, WRUP, was not heard at the camp site near the lake, and frankly I forgot to change over to it while driving through the city on my way up to Christmas.
WPIQ-FM Manistique MI was not heard, although I tried for them at the camp site using a Sony ICF2010.
I was impressed with WNBY AM/FM. Both sounded live, reasonable spotload, and had a fair amount of public service. AM is County, while the FM is oldies. The FM dual IDs as Newberry-Sault Ste Marie which was kind of a stretch for me. While in Sault Ste Marie the signal picketed badly, and was lost about 10 miles south of the Soo.
WMJT-96.7 in McMillan (ripshot of Newberry), also sounded good with the slogan of Eagle, and "we play everything". I heard everything from Patsy Cline to Phil Collins which was not disturbing to me. The only thing that was a bit of annoyance was one of the DJs named "Casey" who was boarding on being a "puker" in his delivery. Overall a good sounding station.
My bro-in-law, being a county fan, camped on 102.5 WCMM "The Moose" in Gulliver. It was an exceptionally good new country station, equal to what I've heard in larger markets. WNBY-AM tended to skew to the older "traditional" country.
WKHQ-105.9 in Charlevoix was so-so. I liked them better in their early years, late 70s. I found their ChR format somewhat of a bore.
WIDG-940 in St. Ignace was All Sports when I listened, and if I wanted to hear guys argue and one up themselves, I would go back to work, so it was a short listen. Same with WMKT-1270 in Charlevoix, both of which had horrible signals. 940 was barely heard in the area, and after 7PM at night WMKT was getting hammered by WXYT out of Detroit!
The girls had WLXT-96.3 from Petosky while we drove to the ferry to Mackinaw Island. It was a nice sounding Lite Rock station, live, with a reasonable spot load. One thing that impressed me on the day I listened was that they did Amber Alerts, while others stations (WBCM, WKLZ, WCMW, and others) didn't. I carried a portable with me on the trip and was channel hopping.
WJML-1110 in Petosky was doing sports, and had a so-so signal where we were. I noted that in the early evening that it sounded like their ground wave and the sky wave were mixing to produce some distortion. Also, in late evening, just before their power cut, WTAM from Cleveland was hammering the crap out of them with IBOC. WTAM must have been working on something but it was going on/off at the TOH, which really showed the effect of out of channel emission IBOC has. After they went to night power, 10 watts according to my notes, they were gone.
AM reception where I was could only be described as dismal. Nothing was coming in at all from Manistique, Sault St. Marie, Escanaba, etc. FM was somewhat the same way, but when I was sitting on the boat in the lake it seemed like all the stations (locals included) would have some spots where they would slip out for a moment.
Not really U.P. news, but while driving back from the upper, I was listening to WOMC-104.3 in Detroit and heard them play a Pams series 32 jingle like WKNR had, and promoed the Woodward Dream Cruise. Man, that brought back some memories of Keener. Dana Masucci was the jockette on while we sat in traffic on SB US23.
After that, we switched on XM for some 50s after the wife and I lamented how good Honeyradio sounded in the late 70s and early 80s.
Anyway.... that's a what I can remember. Oh? The fish? Fishing suxed. Only caught 3 Yellow Perch about 7" long. Better luck next year.