I <3 iHeartRadio, radiopup, and Radio.com apps for my iPhone that let me listen to other stations across the country, and here's a few observations.
Many midwest country stations are much better programmed than KFRG or KKGO here in the LA metropolitan area as many play 80s, 90s, and today. I found one station in Montana playing Chris Ledoux, Patti Loveless, and others I grew up listening to when at my grandma's house.
Best programmed stations in my opinion:
Jersey 101.5 - Jersey's talk station, but in the late night hours they go to a classic hits format with a lot of Frankie Valli and the 4 Seasons and Grassroots mixed in.
WSOC 103.7 Charlotte - Interesting DJs and an excellent mix of country songs have had me listening in the early morning hours out here in Cali
Z100 NY - I like their song previews prior to every commercial break and frequent traffic reports make me feel like I'm in NYC even if I'm not. Elvis Duran's show has a lot of callers and is fast paced, which I like- the topics discussed also interest me. A nice mix of old hits sprinkled in... A nice alternative to KIIS FM en Los Angeles
KCBS 880 - One of my other favorite late night listens that make me feel like I'm in the Bay Area with their frequent traffic updates.
Star 94.1 and Star 101.3 in San Diego and the Bay Area area are KBIG 104's sister stations and much better programmed in my opinion as there is much more variety. KBIG has been trying with a few flashback hits, but there's still a long ways to go for the repetition.
Many of the stations I've listened to in Chicago, Florida, and Phoenix, and Vegas sound very current and not a lot of variety regardless of genre.