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Okay, back. Before actually playing this session: I honestly expect to finish this run either this update, or the next one. Probably this one; there's not much castle left to explore, and item density would need to be through the roof to fill this update before finishing while still leaving enough to bother with another.
Hello, bane of my existence. Now go away.
As you might expect from the Clock Tower, the local boss is Death. What's unusual is that you don't kill him.
The other side of his boss room is an elevator shaft spanning the entirety of the area's height. There's a breakable wall near the bottom with this fun little subweapon.
The shaft itself isn't devoid of items, either.
Though it is more trash than treasure this seed.
Remember Black Panther from Aria of Sorrow? This is basically that.
The first item in the last section of the castle is, somewhat appropriately, the last worthless buff spell.
This thing I'm standing on broke the floor to make an alternate route here. I don't really need it; I have no intention of leaving until I find the boss warp slab.
Even more summoning.
Worthless shoes in a secret room.
Well, found this cutscene. That means I've found the last few bosses. Time to backtrack to the Grinding Room to level up my subweapons.
Stopping by to Sanctuary the shopkeeper real quick, I am first greeted by... whatever the hell Jonathan's saying here. 
The shop's also expanded his stock a bit (not pictured: Knife for 2000 and Hex for 19000). Near as I can tell, that Vampire Killer he's selling is Richter's.
Offloading the equipment that keeps dropping from enemies gives me plenty of money to buy some Master Rings and the subweapons. Now to go practice them...
I forgot to check down here in my test run. Turns out I wasn't missing much.
Okay, enough stalling, time for the final boss rush. First off: The Sisters. Naturally, I Sanctuary them to obtain access to the others. Unfortunately, they're disagreeable and do thoroughly disproportionate damage, so I go through basically my entire MP bar before they deign to let me actually cast it even with Jonathan playing decoy (they focused on Charlotte more often than not), and I needed to use a Foie Gras just to survive long enough to cast because they casually tossed out a 500-ish damage attack and spammed 50's by the end. Gonna head back to heal and replace my food before moving on.
Just to be thorough: Whip's Memory. Like vanilla, he's weak to Dark (though he traded his Holy resistance for the entirely reasonable Whip); unlike vanilla, I have a better subweapon to exploit that weakness.
No, the upgraded Vampire Killer isn't very good. And yes, it's got different stats from the one in the shop; that's why I think he's selling Richter's.
I forgot for a bit that the second portraits of each theme are here in vanilla, so there'd be items here instead.
The helmet is, of course, garbage.
And it's too late for me to bother grinding up the subweapons even if one of them wasn't the Grenade.
Anyway, Brauner. Weak to Whip; kind of appropriate, considering how the most prominent whip in the franchise is an anti-vampire artifact.
There're a few items lying around in the area unlocked by killing that usurper.
Naturally including useless equipment.
And a spell that comes way too late to be useful.
And a false ceiling immediately before the final boss. At least there aren't any new subweapons here; that'd be insulting.
Last boss phase 1: Dracula and Death at the same time. My first attempt they hit me with a cheap-shot Demonic Megiddo (their full-room instakill combo); the second time I just control Jonathan and focus on Death, leaving Charlotte out of the fight to preserve MP for Phase 2.
Last boss phase 2: Dracula and Death merged. Ironically enough, weak to Dark. I try to Dark Rift him, but the fact that it only targets directly above you kinda gets in the way of that, and Valman-weapons aren't very useful in the AI's hands so I need to control Charlotte (and thus can't aim Jonathan's Shuriken properly). Regardless, it's easier than Phase 1 because he doesn't Demonic Megiddo me.
That's Portrait of Ruin Randomizer completed! For those of you who want to try it for yourselves, remember my failed run and keep in mind that not every seed is actually possible despite the logic because the randomizer itself is unstable and/or they haven't filtered out whatever enemy causes the crash.