Some others in this thread have noted that there might be a credentials "arms race" going on—I would add, in particular, in healthcare, education in government, per Tyler Cowen's book The Great Stagnation: How America Ate All the Low-Hanging Fruit of Modern History, Got Sick, and Will( Eventually) Feel Better. Parts of big business may have signaling / credentialing disease too.
Bryan Caplan is writing The Case Against Education, and he argues that too much of education is a signalling arms race. Here is one introduction to his thought: http://econlog.econlib.org/archives/2015/04/educational_sig_....
Also, you should not that in many cases consultants in other professions often give full resumes including education (even pictures) in their proposals to RFPs, I would think you would be familiar with that in your work.
Anyway, as far as the "can you do it" stuff .... I think HN too often writes off university as a place one might learn "how to do it" .... Oh well. =)
In software, more supply = hiring people who can just get the job done and not worrying so much about credentials.
And yet, we keep hearing about the constant shortage of programmers. Hmm, I wonder why that is . . .
You can easily hit a wall even with all the books and MOOCs at your disposal, due to having to do all your learning after work when you're tired or on weekends.
To have to go into debt in order to work on interesting things is unfortunate; just how many people who could have made interesting contributions in a variety of areas never do so because of that?
Studying yourself into web dev and such is eminently possible, but if you want to do, for example, deep learning work at even one-half the Richard Socher-level, you almost surely need to go for an advanced degree. It might be different if you're a superhuman autodidact rather than just a "standard" one, but there are a lot more of the latter (a set that I include myself in) than the former.
But there is far more demand for standard development/architect roles and even those roles command a generous salary.