... my general thought process is that if your company is willing to pay for even a decent portion of it, do it. Right now your job situation is good and steady. And from what I understand (and you touched on this) IT jobs are not super difficult to find if you're established in the industry.

But if shit hits the fan whether due to this horrible administration or some other reason, and you *can't* find a job as easily, it's good to have that piece of paper to stick out against other candidates.

But again, for me, it would depend on whether or not my company was willing to pay for it. School debt sucks.