The only flaw I see is in your assumption that the Trial takes place during the Oblivion Crisis. After that premise is refuted, your argument breaks down into "I think it svcks, and therefore it's wrong, and the Loveletter should be too!".
I mean, seriously, this threatens to overshadow my level of ignorance (which amounts to over (1+0+0+8)*1000), and we can't have that. Only I get to make myself into a various assortment of asses around here.

This thread made me chuckle.

As for the canon level of the Loveletter and the Trial, they both are. The Loveletter has, as Lady N said, either been averted by the actions of Sul and Vuhon or, also likely, was simply us blowing the events out of proportion. I've done it before, and prophecy never has a sense of scale. As for the trial, aside from being several long-standing series writers working in tandem on a single project outside a specific game (alas that it doesn't happen so often any longer) it does provide as good an explanation as any for the disappearance of Vivec. If you don't like it, assume it was one of the other ideas presented in Oblivion and be done.

As mentioned above? You mean as YOU mentioned above. The texts say NOTHING about the Oblivion Crisis. The only logical conclusion is that they happened before the crisis, which would also make sense because the trials happened far before we even knew about Oblivion being in the works.

As others have mentioned MK was only involved in it, he was not the sole creator. Many, many people were involved, and to call them all liars is to call just about every lore developer a liar.

Yah, cool story bro.

A little study on the topic of subjectivity might do you some good.

Although this is irrelevant: if Azura wasn't able to attend to her shrine, she wouldn't even need a minion with a similar voice. After all, she's a Daedra Lord. She doesn't necessarily have any specific pitch and tone; she can sound however she likes.

Unfortunatley, I find it hard to belive simply due to the way Azura is perceived as cowering before the might of Vivec? She was out to destroy everything he created and lift the ban on the lies. Doesn't seem fitting ?

She manipulated her way into a minor coup by poking holes in prophecies and exhausting a line of weak mortals. Not really a dominant force on the Mundus. Then, revenge. Seems fitting enough.

Daedra hate the waters of oblivion. It's a pretty terrible place to them and changes them. So anyone knowing their neonymic along with the protonymic is pretty terrifying to them. When used in combination, their energy is drained away and they are banished to oblivion.(The end of Battlespire demonstrates this with good ol Dagon)

Is it worse to die and be reborn not knowing who and what you were in your past life, or to die but having your soul remain conscious of the surroundings, feeling an ever present and gnawing cold eating away at your willpower with all of your senses completely deprived?

The daedra may be "immortal" but wandering the waters of Oblivion is an extremely nerve wrecking experience, which is why lesser daedra flock to the princes for protection and fear their retribution.

I somewhat agree, and I both love and hate that part of the text. On the one hand, is the power of a Daedra Prince(ss) not at least equal to that of pretty much any other active being in TES lore? On the other, it's a reminder of how very complex and fallible the natures of the setting's "gods" are, and of how much mastery can be gained and how many changes wrought by the hand of a (once-) mortal.

More on-topic: isn't pretty much any Elder Scrolls fiction MK writes considered to be canon? And if not... why not!?

I can take or leave a lot of MK's stuff. His contributions to the universe can be overstated, so I somewhat understand your frustations. That said, if you're going to make a point that hinges around chronology, the first step would probably be to prove the chronology. Instead of finding evidence that Uriel was at the trial, you might look for evidence that it happened after Oblivion. I'm not seeing any.

As for Azura, her speech in Oblivion was recorded on a 1984 TEAC dual deck cassette recorder slightly before the events of Daggerfall and placed near the shrine by her followers. If you listen closely you can still hear elements of the Men Without Hats mixtape she recorded over. This is confirmed in the Loveletter.

That's a fun spin on things. I like it.

The ideas expressed and used in them will be recycled (usually by him when he writes officially), or they're expressing ideas not explicitly in-game, but forming the backbone of the world described in the mysterious filing-cabinet of Dev-Design-Documents. So, they're as good as canon, but not technically.
A more hardliner here will say "Yes, it absolutely is canon," while an Anti-MKer will say "They're nice, but no they're not.

Others will say canon is simply Todd Howard and team's Tamriel, not ours.

The problem with this thread is not that someone wants to discuss non-game lore (for want of a better term), but that the tone on both sides is confrontational and - in some cases - disrespectful.

Telling people they "can't handle" your opinion is extremely rude, and any reactions in a similar vein are just as uncalled for.