And the problem with this is???
For your situation, it is the best of both worlds, you are getting work experience and tuition benefits. As person who completed 3 Masters and helped hundreds of employees obtain a degree/advanced degree on the Corporate dime, there is nothing wrong with seriously thinking about this as an option. You are going to have to eventually work some place anyway. You can work hand in hand with your manager and HR to formulate a career plan for your next job as you are obtaining your degree.
You need a concrete plan for paying for college, not a bunch of ifs/thens.