Lost soul here . . . first time using Illustrator

For version CS5 you should still be able to get "Real World Illustrator" by Mordy Golding. That one is an awesome foundation to learn not only simple recipes on how to do this or that, but it teaches you how the application works. Version CS5 has the functions you need and it's a good basis to learn the app. And when you think it's time to move to a newer version you can totally do that with that setting of CS5 and "Real World Illustrator".

Regarding your question for truly educational content, you have some good books, and also complete video courses, not ramdomly picked up Youtube videos of varying quality, value, etc. We read a novel from the start, not jumping across pages, right?

Well in Lynda.com you have excelent courses, using current and previous versions of Adobe Illustrator.

The basic core concepts have not changed, so you can follow general contents of any version that interests you. 

Finally, do not lose your time playing with the program (any program) without some guidance from a book, video course or a helping friend or online or presencial classes, not worth the effort and time it needs. 

It may not be worth learning on such an old version you can no longer buy; you also are less likely to find targeted videos. If you're completely new, an up to date video for something 8 versions later is likely to be frustrating at best. You can subscribe month by month for $30 (don't get the "annual, paid monthly" $20 plan).