I recently made a 95 year old human cleric with Alzheimer's, dementia, shizophrenia, anterograde amnesia, night terrors, and paranoia.

Part of the character was that he brought along a paid "guide". This guide would remind the elderly cleric several times a week that he forgot to pay the guide this month's salary. The rest of the party, in character, were furious when they found out. Out of character, they were kinda pissed, too, but not at the guide.

They were pissed, because one guy had convinced everyone else that the character with the highest wisdom should be the keeper of the party's money.

You listed like three different mental disorders that would effectively lower a characters Wisdom score. I'm guessing the rest of the group dumped wisdom, which means that was an entirely in character move for them to trust you.

Fighter, barbarian, and a bard. My character got a nice wisdom boost for his age. I argued that he could still act with wisdom from moment to moment, and he was still the same kindly old man he had been before, the only difference being that he needed someone to keep him on track, thus, the guide.

Either way, he still had a wisdom score of 22. Now, due to his anterograde amnesia, his int was capped at 10, since he couldn't learn anything new.

He was literally going on one final pilgrimage to a holy temple where he could kneel and pray one last time before he died, and so he could be entombed in the great mausoleum.

Once has the party encounter a Wyrm class black dragon who was insanely messed up. Blinded, all limbs aside from head removed, massive amounts of ability drain and negative levels to represent the sheer volume of injuries he’d taken. Really the only things working were his voice and his ability to shoot acid. The party found him imprisoned by a clan of ogres who were farming him for his acid.

Turns out the dragon also revealed a major plot point, namely that the party was in the future, since this dragon was the same hatchling who the party helped retake his home from some goblins early in the campaign. I intended for this to be a really poignant moment, as the party was actually quite fond of the little guy (he tried so hard to be a big scary dragon, but was really just tsundere). I wanted them to have to deal with possibly mercy killing an old friend.

Then the cleric pointed out he now had 7th level spells, and a scroll of Greater Restoration. About an hour later the party had a VERY powerful and VERY angry ally in their fight against the Hell invasion that had occurred in the 1000 years the party had missed

That is exactly why you should take advantage of every opportunity to ally with any boss level monster not affiliated with the local villain.
Sweet, sweet demolition.

Outstanding play.

you know what's going to be fun? trying to read what he wrote during this session when preparing the next one.
The things written while half-asleep will be hard to decifer.

Wait, this is your comic's anniversary too?! Congratulations on eight years! Whoo!

So Cory becomes scarily well-adjusted and competent when sleepy. Makes sense, if he’s the type to prioritize staying coherent above all else when picking brain functions to drop; leads to some savant-level eye-on-the-prize tunnel vision.

appy anniversary. that's some nice longevity.

This arc makes so much more sense in this context.

I kinda hate this arc in the show. It's dull and boring.