Social media goes on forever and the training never ends

My job moves a little slower then most marketing design jobs. Working in books we market and advertise a lot of stuff via paper. We print a lot of words on paper, we advertise on paper. Recognize! I'm getting into that whole digital space, but I will be the very first to admit I'm behind. Yes I've been in that digital space for some years, and yes I know front-end Flash. But banner ads and facebook profiles are really the extent of it. Truth be told, I'm more comfortable in the printed world. I would love to move completely to digital and online—I don't need convincing as to why but a reassurance that it's worth it is appreciated.

Todays extensive training on online advertising brought up a lot of interesting points on traffic I'd never considered. Our VP pointed out that a lot of authors/agents/editors like seeing actual printed pieces. For example, a full page New York Times ad is deemed an accomplishment. "I'm a big name author, here's my big budget ad in a big national reputable newspaper." But she pointed out something very important, what did we, the publisher and by way of that the author gain from such an ad? Who saw it and what did they do after they saw it? Did they move on to the style section or run to Barnes and Noble?

I've never thought about that. Maybe it's because I've been trained not ask. Or maybe it's really because I don't necessarily care. Either way it did spark an interest. I know that people see the stuff I do, we've basically got that revelation covered. But what I show them, what they see, does it have an effect? Are they following through or simply going "Oh that's cute/sucks/is irrelevant/life changing."?

The good thing about online advertising is all of it is tracked. We know how many times someone clicks on something and where they go after. We know if they buy something, if they simply look at it, and creepily enough, how long they look at it.

I once looked at a pair of boots on Zappos.com. I didn't buy them because I didn't have enough money for them. Every time I was online, an ad featuring those shoes followed me. They haunted me, ok more like taunted me. Buy me Sarah, I'm so awesome. I'm a little black suede bootie that would look super hot with dresses. It took a few weeks but I bought them. What's the parameter on this? How far can tracking clicks and ads go? I understand the appeal. In theory I can show two ads at the same time, and see if one ad gets more relevant feedback then the other. And I'm exhausted at the very idea.