You keep assuming the worst case about student debt. What about going part-time to U Chicago, and having a firm pick up the tab, like our ubiquitous other two people? And, well, working summers? Or getting a scholarship? Law school doesn't have to be a debtors prison where they brand your thumbs when you leave. Of course, you can work at the PTO and go to Georgetown, but then you have to compete with people who worked in law firms and can already draft patent applications. Just see how far PTO experience without working in a law firm will get you these days. If he works for the PTO for 2 years and leaves, then fine. But a lot of people at the PTO started out strong like, him, and ended up, after ten or fifteen years, tripping over their feet and falling down manholes. The only reason you see attorneys there now is because of the job market. During the tech boom of the early 200's, the PTO lost more than half of the examiners in a short period of time (2-3 years, as I recall, with a 17 percent turnover).
A U Chicago degree is something to be proud of for life. Having once worked at the PTO just proves that you probably can write an office action that combines a glass of beer with a shovel.
Anyway, sorry about getting personal, I won't use the phrase numptyland anymore.