Sound like you are on the right track, and increasing your technical chops is definitely a good way to get to where you want to be or to at least give a better impression to potential future partners.

That said, sounds like from this line:

>I want to make sure if I do leave my job it's the right thing to do and that I don't spend months without an income and end up with nothing to show for it.

..that you are not ready to quit your job yet. It's a fairly high probability that this is exactly what will happen. If you aren't comfortable with that fact, then you don't have the risk tolerance necessary to go for this. At the least though, I can say that if you do go through with it, no matter the outcome, I highly doubt you will think you 'wasted your time'. If you look at the report-backs on HN of those who have failed, almost everyone has learned some skills and life lessons that made up for the experience.