I'd think an applicant would want to cast a wider net and then escalate investment in individal openings as hiring companies signaled some mutual interest.
Maybe some rules of thumb are in order, i.e. x hours for an application, 2x hours for a first interview, etc.
He only needs to change a few names & characters to use the same awesome application for different openings.
Heck, the only reason I haven't quit my job yet is I'm working on something potentially impressive right now that isn't done yet.
Even if someone is good at their job, I'd never hire some run-of-the-mill joe who has zero creativity over someone like this, who thinks outside the box a bit and gives something like this a shot.
It's certainly not a trend, we're just seeing a lot of these unique approaches to being employed recently on HN.
However, at the end of the day, the only thing it does is calling attention to your resume/portfolio, and making sure the company knows you're very interested. (rather than being one company out of tens to which you sent your resume) But if the resume/portfolio doesn't interest them, it won't change much.