Regarding the degree, it's all about the job you're looking for. For most web dev positions, experience is definitely more important. The advanced degree will come into play if you're working on innovative backend stuff: refining fuzzy search algorithms, high demand storage mechanisms, or anything else that sounds particularly Googley.
There are some really interesting sounding positions out there that will definitely require more formal education than most of us have time to acquire. But, most listings just require that you're basically competent. And basic competency isn't well-tested in the classroom; it's proven in the field.