Thoughts on unfunded programs for better job prospects?

When applying to graduate programs, the typical sentiment is that it is unwise to go into debt for a graduate degree because, due to lost wages from not working/not advancing a career for 5-6 years, one comes out of a program ‘doubly in the hole’, so to speak. Since even a funded program has real world costs in lost wages, these costs should not be compounded by paying large tuition amounts, especially in pursuit of a tenuous job market that is likely to leave one jobless in the end.

But, for someone who wants to go into academia in the humanities or social sciences where jobs are so scarce, is this really wise? Say someone could get into a masters program at a top school, perhaps one in the UK or the US, which isn’t funded but is regarded extremely highly in one’s field, isn’t it worthwhile to take on debt for a program like this because it secures a significantly higher likelihood of academic job prospects (vis-a-vis better chances for admissions into top-level PhD programs)? Isn’t that a better move than taking a funded offer from a decent but not outstanding school, and then very likely not getting a job after? It seems to me that one can take on the explicit debt of a student loan, or the implicit debt of a funded program with unreliable job prospects. The former gives a much better chance at paying back losses, but the latter?

Would love to hear from someone who has tried this route with success. Sometimes it feels like the only people who offer this advice (never pay to do graduate research) are professors who got their degrees 15+ years ago when the job market was less abysmal, and people who went into a mid-level funded program and couldn’t find work after. I wonder if there is also a group of those who paid for opportunities (MA programs, visiting student programs) at top universities and managed, through resume additions and/or networking connections, to get themselves into PhD programs with better placement records, who are now employed and paying off their debt, and who we don’t hear from.