Having a higher degree or two is all very well. The only way I would actually consider it to employ somebody is if they were totally equal in every other way. The fact of the matter is most people can do a Masters if they want to. It would only add value to a candidate if it improved their practice. How would a masters improve your classroom environment? In many ways it can, but you would need to be sure you could evidence this when applying for jobs. My second masters is specifically leadership related. It allows me to reflect on my own practice, giving me ideas for improvement. The amount of reading I have done regarding best educational practice and reviews on critical incidents give me an idea of how to handle specific situatons. You need to show how you have put this into practice for a masters to actually mean anything. In short, a masters is a piece of paper, it is what YOU make of it that will make you more employable at senior level.