Speaking as someone who's gone through this process with visa sponsors etc. - I feel a little ambivalent on this.
Would it have been a big deal for someone at the front office to write the date down in a diary? No.
And you'd like to think their lawyer would have emphasized to him that this was not something to fuck around with. I am totally amazed that he overstayed his visa. From Homeland Security's point of view it's not just a paperwork mistake. It's basically saying, "Yes I was a bad boy in the past, but I've reformed and I understand the gravity of you letting me into the country. I won't violate that trust." And then instantly violating the terms of entry...
But those things aside, ultimately the visa page is in Luke's passport. He's the one who has to convince the people at the embassy and he's the one they'll look at as having been cavalier with his visa.
I had eight years of this sort of processing before I became a citizen, and being aware of the precariousness of my status affected lots of small decisions I took in daily life - and I always made sure I was out of the country when I was supposed to be. Yes, I had legal help from my employers, and could ask advice from my lawyer, but at some point it was on me to take care of the most basic item of business. It's noone else's life.
AND if I have to change my avatar again I will be mighty annoyed...
"I guess everybody has their own thing that they yell into a well", Bill Callahan
It's the hope I can't stand.