It's a pretty nice market to be in radio, and I've been offered jobs at every radio group in town. Most of the air talents are older and have done other things in bigger markets but wanted to live in Bend. A lot of what goes on in Bend doesn't sound small market.
All the groups have their pros and cons. Keith Shipman is a really nice guy at Horizon, but I've heard the staff tends to be extremely multi-tasked.
Bend Radio Group used to be a nightmare because of a crappy OM, but they fired him several years ago. I know many of the on-air folks there now, and they seem to like it. I think it's a much better place to work now.
Combined is full of people from big markets who wanted to live in Bend, and they are just having fun. Very low turnover there.
Small owners who don't limit creativity: That's how I'd describe Bend radio. I did corporate radio in a Top 5 market, and I walked away. I came back to Bend because I wanted to. I've been offered jobs in bigger markets since, but I'm very content to stay here. I'm much happier in Bend without the BS, and sadly, make more money here than I made in Market 5.
It's also a great market to freelance from. I mountain bike, work. Ski, work. Raft, work. Housing is outrageous, but if you just accept that you're going to rent, it's fine.