I’m interested in transitioning from web development to machine learning.

My math background is mediocre (basic calc) and my only programming experience is in web dev technologies (3 years). I want to be realistic about my effort level and opportunities. I probably won’t be going back to college, but have 10 months left on a work contract and would like to spend any free time learning the basics.

1. What is the feel of competition in the field? With my time-frame and background, is it reasonable to think I can earn an entry-level position?
2. I’ve heard the field is broken up into data science and data modeling. Is data modeling more programmatic? Will my experience as a dev be more relevant there?