I think this guide is already failing people by assuming successfully initiated conversations and labeling it as "basic". If you have plenty of social contacts, that already warrants being considered "intermediate".

The really difficult things are maintaining good first impression and talking to (perceived) strangers. You know nothing about a person until you talk with that person, so what exactly are you supposed to do? There is a bootstrapping problem.

Classified ads are a good example. It's not like ebay, where you click a button and the delivered product is guaranteed to arrive a few days later. Instead you get a blank form of nothing, where you can write whatever you want and there is always the possibility of rejection. It's very much unlike any store you've ever visited, where money is king and the customer('s money) is always right.