I'm currently a college student working towards an elementary education degree. I am also looking into getting my masters, however schools won't hire you if you don't have any experience b/c they would have to pay you more and without any experience you're a bigger risk. I am looking into programs that you get two years of experience while getting your masters... benefits to this is they place you so you don't have to search for the job plus your pay/payments kind of equal out so it's not a fortune. The down side is there are none of these programs, that I have found, in Iowa, I think Minnesota has one but that's another thing to consider.
One other thing to consider is that a person can get their course work done for the masters, but not finalize the paperwork and delay the actual granting of the degree until they are securely employed/reach tenure, etc . If you are unemployed, you have more time on your hands to do the work, but not the income to pay for it unfortunately without loans. The programs I have seen give you seven years to finish the degree from the time you start it.
I teach and had a bachelors, masters and doctorate when I was hired for my first job three years ago. I also had a ton of experience in the real world which made my resume stand out I guess. I was hired at one of the best schools in Minnesota (ratings-wise and test scrores-wise). I was recently told by the man who hired me that they wanted me due to my experience, but if I was looking for work these days as an inexperienced teacher with heavy education, I would have a hard time being hired due to the extra $ demand my degrees bring with. Very glad I got in when I did.