If he did and still couldn't find a job, I just find that interesting.
If he had 50k, in my opinion, then it might be a commentary on the meaning of the reputation, but not so much as is.
He may not be a Jon Skeet but he's clearly head and shoulders above the great majority of StackOverflow users. He's exactly the type of programmer that I think Joel would say would have a good use for the Careers portion. So I find it interesting that he had such a hard time finding a job ASSUMING he knew about and utilized the Careers section.
... but he did have a pretty desirable skillset with stuff like C#, .NET ( I see ads for this kind of thing, anyway). And F# which means he's gotten into the FP stuff which means he's aware of current trends. So if it was tough for him to find work, well, then it's tough out there.
Oh, and nice to know that I'm not the only one who has trouble with nervousness during interviews.
On top of that, I have no doubt that if he emailed the team at StackOverflow and told them his situation, they would have gladly waived the fee. I just don't see the money as being a sticking point.