Scott,
I, too, have a good deal of experience flying r/w. What I found interesting is that you scoffed at the mention of my bringing up that there's absolutely nothing wrong with direct destination airport during a low-traffic environment. Aircraft (yes, even the tubeliners that everyone on VATSIM is so fond of flying) go direct destination every day into smaller class C/D fields that don't have SID/STAR procedures, and also into Class B primary airports late at night on the mid-shift, which incidentally is the only time most of us issue said shortcut. Said procedure simply requires the pilot to (gasp!) PLAN A DESCENT ON THEIR OWN and maybe be a bit proactive in requesting an approach or planning self-vectors if there's no controller online, which would be the same whether or not he's on a STAR. Unfortunately, that requires a bit of situational awareness, which is sorely lacking not only on the network, but also within the pilot population for which I'm responsible for training at my real job every day.
If it's a REASONABLE pilot request, I have no problem turning it down. I have no problem leaving a guy who is unable or unwilling to re-program on his flight plan either. I just find it funny that we're the ones always being taken to task about not accommodating pilots, when there's very little most pilots on the network are willing to do to accommodate a controller.