I'm a bit unsure about this addition: Air America.
Two concerns: the entry looks to be merely using this article as a political soapbox (in which right-wing bias in media is fine, but supposed left-wing bias is not) and it also looks to be completely off-topic, if this trope is about a comical, low-budget, shoestring operation being Played For Laughs, WKRP-style, and not merely a list of every station to have ever gone off the air in the history of broadcasting.
Yes, broadcasters fail for many reasons. Some were poorly run, some lost their audience to a more-powerful competitor, some fell victim to the siphoning of content away from free OTA TV by pay TV operators. Some were in markets too small to sustain them, or couldn't get a viable network feed. A few fell prey to the Great Recession of 2008-09; in some cases, this and the digital TV transition landed together as a double whammy. A handful of stations signed on in analogue soon after the turn of the millennium, only to have to go digital by 2009, by which time they were wiped out in the economic recession. Equity Broadcasting (which owned many underpowered UHF terrestrial stations, all fed from a Central Automated Satellite Hub in Little Rock, Arkansas) was one particularly dismal example. Then there are the stations which failed due to flawed policy from broadcast regulators; uhftelevision.com records a long history of failed stations from the 1950s and 60s, for example.
There's a whole graveyard at wikipedia:Category:Defunct broadcasting companies.
And yes, it's possible for a broadcaster to fail after experimenting with deliberate right-wing bias. In Canada, CKXT-DT and its Sun News Network make a prime example - although the CRTC's unwillingness to allow a terrestrial station to simulcast on a speciality channel didn't help.
There are many dead stations, but very few of them are memorable as comic relief. Most of the business failures are just sad - especially if they leave a community with no broadcaster or no OTA TV at all. As such, the majority do not fit this trope - which is about content, not merely the fact that a broadcaster went broke or faded to Dead Air.
The current Air America entry looks like political soapboxing. I just don't see the humour.