If you (as consumer) are willing to tell us a few things about yourself (location, sex, age, one or two interests) think it will also allow us to deliver content you're more likely to enjoy.
Evil?
A little. I personally wouldn't want to give any information, and this is where I think you could hit problems. Sure, targeted ads help the marketers. They don't waste money on showing ads to people who aren't interested in their products. I think saying that it's for "my benefit" is a little like the RIAA saying that DRM is to help me.
It's not for me. It's for them. Call a dog a dog.
Yes. It does allow you to deliver content I'm "more likely to enjoy" but the fact of the matter is I can choose my own content that I'm likely to enjoy by selecting the podcast I want to view. I don't need you (or anyone else) to tell me what I'm going to enjoy. Plus, if you target advertising individually it accentuates that which makes advertising evil on it's own. That is, it's capacity to control our minds. Overly targeted ads can quickly become extremely difficult (if not impossible) to resist.
Then we're not free. We're buying machines. (It's already very close to that and I fear any small steps in that direction).
I, personally, wouldn't go too far towards the "personalized" route. At least not by asking the customers to volunteer information. It just won't work. First off, imagine the backlash from groups like the EFF (and not all publicity is good publicity -- that's a fallacy, just look at Rockstar Games). Secondly, they won't do it. Look how people react to AdWare (and Real and on and on). It's been tried over and over again in this "internet age", and it's never been the success that the buzz seems to suggest. The reason for the people to give up that personal information has to be
far more compelling than simply to tailor ads to them (so they don't see ads they don't like). People
like to see ads for things they don't want to buy (because it gives them time to go to the bathroom and something to "not pay attention to" and make fun of and feel superior). It may work for a few, but the vast masses will not give up their information without a compelling reason.
Google's model is far more palatable to the public. They "personalize" their ads not by asking you for information, but by collecting information based on
what you do while you are on their site. Its a small, semantic difference but the implications are huge. One way (the way you propose) requires active participation from the customer. The other (google's) only requires passive participation (and provides a way to avoid it -- clear your cookies regularly).
It seems odd to me that on the one hand you like a technology that allows you to skip ads (Tivo) and yet applaud one that allows a content distributer to insert ads.
I don't think this is at odds at all. I don't have a problem with them putting ads on TV. I do have a problem with DRM that prevents me from doing what I want with my media. I do not buy the argument that it is their media (and that I'm a licensee) at all. I seriously doubt that the framers of the constitution would have either (of course, they wouldn't buy our current copyright term length either).
As far as the distributer argument.... I'm not sure I follow you. The whole promise of Internet-based broadcasting is that you can self distribute your work and do not have to go through a media conglomerate to reach a large audience. If your work is compelling enough, they will come. Sure, there may be indexing services. However, as a content producer, I am certainly not going to let the indexing service take control of the advertising in my production (or especially the money from said advertising).
Some people might allow it, but as the medium develops, I doubt we will really have many traditional "distributers" as you describe. Bittorrent just makes that unnecessary. The only reason we need them at all now is so that the content producers can make money (the distribution site has ads and makes money off of user contributed content). That's, IMHO, a quick-fix because there is no solution such as what JRiver proposes. Anyone moderately interested in distributing commercially viable works will not accept a similar situation.
And did TV end Radio? No, but it certainly changed it drastically and greatly reduced it's relevance. Ask your local theater owner how they feel about DVDs and home theater systems. I'm not saying that this should be the only model... Just like ad-supported TV isn't the only model (HBO and PBS are the channels I watch the most at home), but I do think it's an important step for the medium.