From diploma to bachelors to masters

The ongoing debate/new status quo has been that a bachelors is the new high school diploma. They say without a college degree you won't be able to do anything more than work fast food(exaggerating yes I know but that's the point high school counselors try to make). Then everyone went to college to get degrees and for a while they all god jobs. Now there's this huge pool of college graduates fighting for a finite number of jobs. So a select number of them move on to obtan their masters to separate themselves from the crowd to get that job. So what happened next? everyone is going for their masters making it the college degree of 10 years ago. At what point does this need to set yourself apart by overachieving begin to devalue the worth of a college education. Even more importantly at what point in your life are you able to break even on the cost of that degree? I myself am a fairly educated Gen Y'er, I finished undergrad with a B.A. in graphic design and B.S. in Instructional Technology, finished all my graduate coursework for my masters and just need to complete the thesis portion(but that's blog for another time). Here I am, 2 and a half degrees later, more than $45k in debt and in my first career that brought me across country. By the time I have these loans paid off I will be more than halfway to my mid-life crisis, is that when I'm going to enjoy the fruits of my labor? Likely not, I'm sure I will be onto a mortgage payment by then. Could I have just gone to an ITT Tech type of school to become a train locomotive engineer and been just as happy? You tell me, was all the hype of college worth it for you?