The web today is essentially one big advertising stream. Everywhere you go you're bombarded by adverts.
OK, I get that it's necessary. Sites do cost money to run, people who work on them have to get paid. It might be evil, but (in the absence of an alternative funding model) it's a necessary evil.
There's a range of implementations. Some subtle, others less so. Personally, I take note of the unsubtle and brash ones, the sort that actively interfere with what I'm trying to achieve, and mark them as companies I'm less likely to do business with. The more subtle ones I tolerate as the price for using the modern web.
What is abundantly clear, though, is how much tracking of your activities goes on. For example, I needed to do some research on email suppliers yesterday - and am being bombarded with adverts for email services today. If I go away, I get bombarded with adverts for hotels at my destination. Near Christmas I get all sorts of advertising popping up based on the presents I've just purchased.
The thing is, though, that most of these adverts are wrong and pointless. The idea that because I searched for something, or visited a website on a certain subject, might indicate that I would be interested in the same things in future, is simply plain wrong.
Essentially, if I'm doing something on the web, then I have either (a) succeeded in the task at hand (bought an item, booked a hotel), or (b) failed completely. In either case, basing subsequent advertising on past activities is counterproductive.
If I've booked a hotel, then the last thing I'm going to do next is book another hotel for the same dates at the same location. More sensible behaviour for advertisers would be to prime the system to stop advertising hotels, and then advertise activities and events (for which they even know the dates) at my destination. It's likely to be more useful for me, and more likely to get a successful response for the advertiser. Likewise, once I've bought an item, stop advertising that and instead move on to advertising accessories.
And if I've failed in my objectives, ramming more of the same down my throat is going to frustrate me and remind me of the failure.
In fact, I wonder if a better targeting strategy would be to turn things around completely, and advertise random items excluding the currently targeted items. That opens up the possibility of serendipity - triggering a response that I wasn't even aware of, rather than trying to persuade me to do something I already actively wanted to do.