Hey everybody! This has been a fantastic thread.
I just started running CoS . I have been really impressed with all of the resources available, and some of the suggestions in this thread have been extremely helpful.
It's been a loooong time since I ran a table top game, and this is my first time running 5e D&D (which I'm now convinced is the best edition thus far), but classic Ravenloft is old hat from the days of my youth

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I started my group of four players at 5th level and brought them in on the western end of the Old Svalich road. It's a little bit beefy to start them at 5th, but being my first time running 5e I figured it would be easier/safer to bump up encounters than tamp them down.
Brining the group in from the west has been really interesting. They got turned away from Krezk and nudged toward the Wizard of Wines, which is just right for 5th level. They tackled the winery and then went to Yester Hill.
I wanted to introduce them to Strahd early on, and so I had his encounter there be genial and non-combative. Strahd came down to meet the party as they walked up the hill. He introduced himself, called them all by name, etc. etc. (They had met a Vistana in the mists coming into Barovia who I had one of the PCs play as if it was her character, so Strahd had gotten the DL on most of the characters). One of the characters noticed the ritual going on up at the top of the hill and realized Strahd was probably just trying to delay them. Strahd, of course, charmed one of the PCs during that conversation, which has already started to sow seeds of doubt and suspicion amongst the players. So things are going swimmingly

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I expect the players to head to Berez next, and then either Krezk or Vallaki.
I've spent some time smoothing out some of the more overtly misogynistic elements of the story, which has led to some really interesting adaptations that I'm excited to play out.
I also love the idea in this thread of the characters working to restore hope to Barovia, so I'm including that in my campaign. In my mind, the characters will be able to escape Barovia once they've loosened the hold of the 'dark powers' by combating the pervasive dread in Barovia, culminated by slaying Strahd himself. The dark powers weaken, the misty borders of the land become permeable, and the character make good their escape.
I figure the powers brought the characters into Barovia (like they have with so many others) to foster new hope for Strahd to destroy, thus encouraging the cycle of dread and despair. Strahd, for his part, is trying to escape Barovia by finding a new penultimate plaything for the dark powers. All in all, not too different from the adventure as written, but it all fits together nicely in my head.
I'm cutting out the Amber Temple and the pass, as well as the dusk elves. Don't need none of that. It's extraneous to the story, in my opinion, and I don't need a dungeon crawl. The characters will have enough trouble with Strahd and the other areas of Barovia.
One big thing I've done is to design a whole new set of encounters in Berez, centered around the church. I like the idea of each community in Barovia having a sacred space that is tainted and which the characters can ultimately redeem. I also dislike the idea of women being killed by their family/friends/community over and over and over and over again in the story.
For me, the whole Tatyana story works better if the 'tragedy' is repeated again and again and again. So for Berez, rather than Marina killed by her own people, I decided to reverse it and have her commit suicide. Lazlo and Grigor know that Strahd has designs on Marina, but instead of killing her they and the people of Berez decide to defy Strahd. They try to reason with him, which fails, and so they prepare to fight him. Grigor does some special priestly voodoo and hallows the church to heck and back, and everybody gets ready to throw down with the Devil Strahd.
Marina knows that this effort is futile, and will only see her family and friends get killed, and so she flings herself into the Luna river. Strahd, however, is royally pissed, not only because 'Tatyana' has once again drowned herself in a river to escape him, but also because the folk of Berez has defied him so blatantly. He's also upset about Grigor's thing with the church, so he floods the town, kills every mother's son, and leaves it as a ruined wasteland to remind folk in Barovia what's what.
Now, Baba Lysaga (hate the name, changed it) doesn't want that sacred space in Berez coming back, so she moves into the marsh to keep a lid on it, which she does by going down into Luna Lake, finding the body of Marina, cutting out her heart, and using witchy magics to further desecrate the church.
This is a secret she keeps from Strahd because, of course, the method might piss him off a bit.
So Marina's "Heavy Heart" is placed on the altar of the church, and it causes the structure to sink preternaturally deep into the mire of Berez, and at a bit of a jaunty angle, too. Only the bell tower is protruding drunkenly from the surface of the marsh.
The characters can access the church through the bell tower, and then have to make their way down into it, going through an attic, then a second story loft, and finally the main floor, which is filled with water. Because of the angle, the water gets 1 foot deeper for every ten feet, making it 10' deep at the far end of the 100' long nave.
The Heavy Heart is protected by a Drowned Maiden, the cursed spirit of Marina, and Drowners (zombies that grab you and try to drown you) created from the people of Berez who took shelter in the church and died in the flood. Marina's goal is to get someone to take her heart off of the altar, but because the altar is submerged in brackish water in a pitch black church buried 40 feet in a bog, her efforts seem a whole lot like she's trying to drown you. And let's be honest, she kinda is.
In the loft is a Caller in Darkness, formed from the masses of people who died in the church, as well as a few Necrolytes, born from some pregnant women who were among those slain. A few shadows haunt the attic, and a trio of Will-o-Wisps hang around the church, trying to entice folks to go down into it and die horrible, harrowing deaths.
Rounding out this horrendous house of worship is the Heavy Heart itself, which exudes an aura of fatalistic despair that gets stronger the closer one gets to the heart. Mechanically, this requires Charisma saves of increasing DC, which when failed cause Exhaustion and a roll on the madness table. All in all, it's probably too stiff of an encounter, but it all goes kaflooey once the heart is off the altar.
The church rises out of the mire, all exhaustion levels go away, the Drowned Maiden is put to rest, the water drains out, and true rays of sunlight bathe the church, killing any other surviving bad guys save for the wisps, who book it for greener pastures.
The characters now have a hallowed church that is bathed in true sunlight during the day, and the Heavy Heart, which is a sweet new magic item that can cast a bunch of useful spells.
The wisps will try to draw the PCs to the church. Lazlo's ghost will give the PCs the whole story and drive them to the church. Baba Lysaga will also 'drive' the PCs to the church if they encounter her (flying in her skull, tossing scary spells, PCs chased by the walking house, etc.). She'll leave them be if they enter the church, figuring that they'll die in there.
Once the church is dealt with, the PCs have a place to rest up, and a handy base from which to take the fight to Baba.
The Heavy Heart is subsequently useful not merely for its cool magic powers, but also for the story. The heart is a strong weapon against Strahd, because it can be used to make him behave irrationally. Once he knows its source and nature, he will want it, and it'll make him angry that the PCs have it.
The Heavy Heart is also something that the Abbot would
definitely want to get his hands on for his flesh golem.
That's enough for now. I expect that my players will find their way into Berez in our next session, so we'll see how this goes!