Hi guys,
I'll start by saying that I'm not posting this to ask for basic balancing tips, as I've that down already. I can create encounters that are mathematically aimed towards a specific difficulty level, as long as they are creative but not insanely complex. Big action oriented guy, minions, multiple medium guys, spicy terrain, simple lair actions, sure.
Now, I love actual plays (D20 veteran), but how dahell do DMs like Brennan and Matt balance their insanely creative final bosses? This fights have VERY swingy terrain features that can straight up murder you, powerful lair actions, powerful spellcasters (a personal bane to balance i have no idea) AND change something basically every turn.
I really wouldn't know where to start to put down the actual numbers for anything here, there are so many variables opposed to a couple damage variables you can average to make a very educated guess on the actual difficulty it will pose.
These fights come up very swingy thanks to all these impediments, without really giving you the chance to average down any expected DPS by the party, and that's just to decide the enemies' HP...
How do you put the numbers down on sheets here?
Even with playing just the monsters in the book, high-level encounters in D&D will be incredibly swingy because there are a lot of abilities for both PCs and monsters where one character rolling well or poorly can completely change whether the fight is a near-TPK or a cakewalk. The party succeeded on the save against the cool boss ability, well they're probably gonna be fine. Or they all failed, well now they're fucked. The boss failed the save and now it's paralyzed, guess you've pretty much won. Or it succeeded, now you've wasted your turn. That kinda thing.
That's why making encounters with a bunch of swingy abilities can actually tip things back into being controllable. If your boss is getting whomped harder than expected, he gets desperate and breaks out the super-kill abilities. Or if the party is the ones getting clobbered, maybe the boss gets overcompetent and doesn't use their super-kill ability until it's too late.
I've found that at the end of the day, the PCs are generally expected to win, and they have a major advantage: when they hit zero, they get to roll death saves and can be healed, whereas the enemies usually just die. This is actually a huge factor in their favor, and explains partially why PCs can beat enemies that might seem way above their level. So honestly I don't worry too much about making strong enemies, my parties can usually handle them. And if they handle it too easily, it's not the end of the world.