I will touch on the negatives first...

There really are not any, an education is an education at any level. No one can tell you it was a waste of time, only you can.

If you are going to go for it then focus on what you want to get out of it and make sure the curriculum the college offers matches to that, if it does not then I would not bother with it. The college local to me does not offer any technical depth or science to a master level in databases, just business side of things. There is one a few towns over from me that I would love to take just for the pure education of it, but the commute is to much to bother. I have come across one masters degree program that I would love to go through at Boston University, and is offered online; just have to find the funds.

You will come across companies that are not going to hire anyone with degree, whether bachelor or masters, without having experience. You will come across other companies that master degree puts your resume at the top of the list. You may not get a job right off as a Senior but should be able to as a mid-level at most.

I can tell you if you are interested in government work (state or federal level) then master degrees are shined upon and in some positions required.