Wait, when you spoke of $2-3k/month, did you mean active or passive income? Because I was speaking of active one - as in, you directly exchange your time for money.

Can't comment on your plan wrt template selling, but it seems you might start earning money faster if you get right to freelancing; though it's up to you, of course.

Speaking of timeline - in my opinion, it might be more optimal to target real-life tasks and not some deadlines: that is, instead of saying "I'll spend 3 months learning JS and then will start creating templates" you might just do the tutorial, maybe make a couple small projects to get comfortable a bit. Then pick some task - like a template, or just browse freelance sites, pick a job you like and use it as a target - start doing it and then see whether your skills are up to it or not. If not, learn more until you get there.

And speaking of money - from what I saw on elance, $10/hr is about minimum for Python/JS, that'll get you people who can barely speak English. Around $15 is not impossible for a person with a bit of experience, and from then on... well, that's a whole different story here, about marketing, client network, connections, self-promotion etc etc. Though, again, for the first couple of jobs there your main goal should be not getting high rates, but actually winning these jobs and creating some reputation.

So to sum it up - why exclude yourself from development freelancing for 6+ months? And relying on templates sales looks a bit risky to me, direct freelance will get you income faster. Though passive income sure is great, so in the end it's for you to decide.

Oh, and seconding jQuery. It's great.