I spent 9 months backpacking from Guatemala to Buenos Aires. There are thousands of people who do this sort of thing every year, and you'll meet lots of expats. In fact, until you hit Colombia, you probably can get by without knowing much Spanish. Personally, I would just skip this article, buy the Lonely Planet and live a little. Some places that I'd recommend seeing:
I would be interested in visiting some or most of these countries in a few years time. At the risk of sounding cliched, I don't obviously want the touristy experience but want to experience the country(ies) and am prepared to do that for a few months. I currently know zero spanish, do you suggest picking up a guide book or should I invest time learning it at a school (I live in SF)?
Believe me or not, they actually have an Alliance Française branch in Granada, Nicaragua, with native French speakers that can teach you the language. Cheap nice place.
EDIT: It's not so nice actually. Go to San Juan Del Sur instead.
In addition to learning spanish, check out https://www.couchsurfing.org/ . If you really want to experience a place than living / hanging out with locals is a great way to start. I've had some amazing experiences through couch-surfing over the last few years and made life-long friends.
I spent 6 months in S america a few years back. Definitely learn spanish! Luckily spanish is probably the easiest language to learn, and you don't really need much. Once your there your skills will get exponentially better due to the immersion.
I did a 3 month after work course (1 3hr lesson per week, plus lots of hw), and then dived in.