I can only say that it is nearly impossible to underestimate the technical unfamiliarity of this audience. Opening the command line terminal is bewildering to them. Not understanding why 'ls' worked a minute ago but not now (it's because they're in the interactive interpreter) causes rage.
You may think you're enticing the beginner by teasing all the cool things they'll eventually get into, but it ends up being a disservice. They're already entering a world of confusion and frustration, no need to add orthogonal concepts to the mix.
If I'm teaching someone who doesn't know how a computer loops in a while loop or what a variable is, then you're advice is counter productive. None of that is useful for them and just gets in the way of what they need. At best you're just impressing them with a flashy demo that they may not even really understand.
If you can't get someone started with the following steps:
1- Go to website
2- Download and press next until the prompt says "Installation Finished."
3- Click here to create a file and save the file on your desktop.
4- Press "Run."
5- See "Hello, World."
You already made it too damn difficult for week one.
All that other stuff is secondary. Getting the words "Hello, World!" (much less getting the screen to show 1 through 10 without dropping into an infinite loop) to show up w/o supervising the student is a huge victory. I can't tell you how long it took me to understand while and for loops, but it wasn't one or two days.
Getting someone set up and running with a semi-significant website is an unrealistic goal to accomplish within a few months... well, if you want that site to be reasonably coded, that is.
People with lots of experience forget that the basics, for a total beginner and near technophobe (as I was 18 months ago), is very difficult. The real "oh, crap" moment came for me when I was first exposed to Emacs. I complained that, in today's day and age, it was utterly fucked-up that some stupid class would suggest you don't use a mouse. I was told that that statement was probably the biggest indicator of my newbie status than all the horrid code I could demonstrate up to that point. Just remember that people aren't ready to learn a bunch of new tools and they aren't ready to give up familiar tools at the start.
Though you do make a good point in your first sentence. It does depend on the goals and the audience. But I think your audience is a bit too widespread. People who have some programming experience are too wide of a net. I think if it were sold as a book for people who havea bit of web development experience then your conversion rate would be higher (from free reader to paying customer).
Now, I'm not knocking on your accomplishments. My approach is merely from the business perspective of marketing you book and videos. Have you tested other approaches? If so, may you shed some light? I used to market/sell books on the web, and find it fascinating. If you wish to continue this conversation through email mine is in my profile.
Oh, you probably just need to tell them to download Pry.