I humbly disagree about the "negatives" about Internet Radio.
I'm a big believer. A lot of I-Net radio is so sloppy, so self-serving and so bad...would you buy an ad for it?
First, Internet Radio is not 5 years out. I think it's today and growing fast. Next month, look for Sansa Connect portable wi-fi radios in the major big retail outlets and online. The units do more than just pick up Internet Radio. Other units like InFusion by Torian getting a lot of buzz. Roku Labs "SoundBridge" (which I have not turned off since Christmas) and A-E Internet Radios now sold by C.Crane and others are coming on strong. I don't think it will be 5 years at all because millions are listening now, albeit teathered to their computers (laptop or desk.) People know what Internet Radio is.
Secondly, Internet Radio hasn't "made a dime" for anyone is subjective at best. Terrestrial AM/FM radio stations stream because it is "cool" and their listeners (25-30 percent at work, according to Edison Research today) like to listen on their computers. The problem: the Internet streams are nothing but "connections" from transmitter-to-listener with no difference than the on-air signal. Essentially, a lazy way of providing "convenience" to listeners, with little involvement by broadcasters. A promotion, in effect.
Third, listener reaction to "commercials" is very negative online. "Typical" radio stations can't afford with brick-and-mortar costs (employees, towers, buildings, studios, transmitters, sales staff, administrative, promotion, etc.) to go without commercials (unlike satellite XM & Sirius...and they charge $13 a month.) So, how to put "more" commercials on to make money on a typical AM/FM stream isn't that easy...or affordable to pull off. Stations would have to sell tons more ads to fill the inventory holes just to cover their on-air spotsets and listeners would probably revolt to hear the "commercialization" of the Internet Radio model. Ads most online don't want to hear. Would you?
Fourth, out of zillions of Internet Radio stations...many well done and, in fact, better than typical "commercial" broadcasters, how many of these "independent" broadcasters really take time to think of Internet Radio as a business...instead of a hobby? Many of these fine streams from all genres are laptops tucked away in the corner of 16-year-old Junior's bedroom so he can play his 350 CDs through cheap software readily available. Is Jr. going out to "sell" his station for a buck? Of course not. So, who's left?
The independent broadcaster who puts a station on "Internet Air" with little experience in selling a radio station, no budget to hire even commission only sales reps and a product still unknown to advertisers because no one's ever tried to sell it with a committment to a target audience, a specific area, or something understandable by most advertisers in the first place is going to make...nothing. Nada.
And fifth, "subscription" Internet Radio through on line "syndicators" is a bit much to ask in the wake of hundreds or thousands of "free" radio stations. Some are so horrible, they aren't worth the price. And people, like in buying cable TV, are fickle. Here today, gone tomorrow.
I think Internet Radio as an entity to compete with AM/FM broadcasters IS possible and realistic. I think the hardware will be there (and is on the way) and municipal Wi-Fi or MaxFi will be made available. (LA's mayor said last week that it will cover his city in two years.)
Typical radio, however, is already screwing Internet Radio with "Flash" players that don't allow stream URL's to be revealed for transfer to portable or off-line units (yet, they want us to listen to the commercials and see their web page ads...

) and with Clear Channel already investing in 400 "channels" of Internet Radio format streams for certain vehicles later this year as well as "smart phones" ... Internet Radio will see profits, if only to a "chosen few" companies soon.
The key will be dedicated education, consumer information and...sales, sales, sales. And did I mention, sales? Ads don't sell themselves and Google's not going to come to you with spot buys just because you're on the Internet. Nor will Live365, MSN, nobody.
It's got to be sold, not just from a nice sounding stream.
Finally, some broadcasters are complaining that they are afraid their on-line streams will be pirated to You Tube or elsewhere, (thanks, Howard Stern fans,) so...what do you do?
You protect the franchise, I guess, and be creative with something worth $elling, for someone to buy and, ultimately, for someone to listen to. Then, you make money.