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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
The Holders Series
The receptionist in Denial is actually the Luck-Based Mission / Only the Worthy May Pass part of the trial.
Almost every Holder has a part where some people instantly fail for some reason. Maybe this is why the Holder of Denial's name is... well, the Holder of Denial, since you have to deliberately not follow a certain instruction. The button has to be there for some reason.
  • I saw that part as the receptionist unintentionally willing the button into existence and changing the requirements for obtaining the Object, since she mentions not noticing it was there until after she started thinking it might be nice if fewer people entered the door since "it must be getting crowded in there by now".

The Holders are all technically in the same institution.
As stated on the main page, the various stories of the Holders begin with going to any mental institution or halfway house. However, when a Seeker goes into said institution and asks for a Holder, they are taken to a place that seems to involve Alien Geometries. It's quite possible that in the world of the Holders, the institutions are somehow connected through gateways to a massive institution that is housed in an alternate dimension, reconfigurating itself so that the Seeker can find the Holder they are looking for.

The Items are in fact Lost Logia
Goign along with the above WMG, the Holders are some sort of Lost Logia cult that collects these artifacts and then hides them in these alternate dimensions, the trials are purely to find candidates who can activate the Logia, and the killing of those who fail is to prevent anything they may have learned along the way from reaching the knowledge of the Time-Space Administration Beureau.

The stories are Schmuck Bait set up by seemingly clever Seekers as an alternate means of getting the Objects.
Any brief perusal of the Holders' trials reveals just how utterly impossible they seem to pass. Anyone who attempts them risks undergoing any number of fates worse than death, and the rewards are minimal (and sometimes are themselves fates worse than death). So why would anyone ever want to go about getting just one of the Objects, let alone all 538 of them? That's what a certain knowledgeable person (or persons) with an interest in acquiring some (or even all) of them asked. So a clever plan was made: why go through the trouble of attaining the Objects, when you can just have some other idiot get them for you? Concisely written instructions on how to acquire each Object have been written and distributed on the internet, with the sole purpose of tempting budding Seekers to set out after them. Then, it's just a matter of finding the Seeker and taking whatever Objects he has, by any means necessary. Mind you, it's not very easy either, but much safer than undergoing the trials.

The Holder of Wisdom is actually one of the most compassionate ones.
By passing the trial of the Holder of Wisdom, you get to know you'll die a horrible death at the hands of someone. You get all the details of both your death and your murderer. Considering that almost every involves a chance of getting a Fate Worse than Death, and some tests are guaranteed to kill you, getting your death predicted with 100% accuracy at least guarantee that you will never get stuck with a Fate Worse than Death. It still could turn that one of the Holders is your murderer, which would make for a really awkward moment once you face him/her/it.
HomestuckWMG/Web OriginalHonest Trailers

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