Advice on career switcher plan

Hello Treehouse Community, I was hoping to get a little bit of advice and feedback on my "career switcher" plan.

Background: I'm a former high school teacher, and I now work for an educational media and technology company (in a less technically-oriented supporting position). I am inspired by online tools like Khan Academy and platforms like Schoology that are pioneering flipped classroom models and other methods of providing students with the best educational experience possible. I also think that the field of education is ripe for disruption, and I want to be a part of that.

Right now, my plan looks something like this:

1. I've completed the Front-End Web Dev track, so I want to spend a little bit of time tinkering with my personal website to really get the hang of working comfortably with CSS to produce a decent looking site. This site will continue to serve as my portfolio in the future.

2. I just started the PHP track, so I'd like to finish that and probably take the Ruby track as well, just so that I'm familiar with both languages and able to explore the strengths and weaknesses of each.

3. I'd like to create a few simple web applications to add to my portfolio... these don't necessarily have to be education-related; they might be "just for fun" projects.

...and then after that, I think there are a few routes I might pursue:

A. I don't think my current company would be receptive to me moving over to a more dev-oriented role, which is unfortunate. However, our developers are working on building out some APIs that leverage our services, so I might be in a pretty good position to work on some side projects in my spare time that are nevertheless related to my day job, and might be proof that I can add value to my company as a developer.

B. I might try and do a little bit of freelancing, starting with people I know and working on building out a side job from there.

C. I might try and transition directly to a more coding-oriented job at a new company.

I think there are pros and cons to each situation, but I was curious if any other people who had been in the "career switcher" role had any feedback, success stories, pitfall warnings, etc. I know I'm really just starting out, but I believe I've found my passion and want to ensure that I am embarking on this journey with realistic expectations. Thanks for any comments in advance!