But he had a bad GPA, so none of the schools offering those programs were options for him. Six figures seems high unless you make some major mistakes, but remember, he is paying tuition and living expenses and losing 2-4 years of salary, experience, and opportunity cost.

I don't think the "school" vs "no school" argument has to be as black and white as it turns into. I think circumstances vary and in his particular case, he probably chose the most optimal option.

And I'd give him some bonus points for beating ("hacking") the system by finding an alternate path to his goal when it became clear to him that his current position became highly disadvantageous.

Also, the community college. In-district tuition at community colleges is typically less than $4000 for the whole year. The in-state tuition at Purdue is about $10,000 per year. Assuming no grants or scholarships, that's $28,000 for a degree from Purdue (their graduate CS program is ranked #20 (us news), not too shabby).