I posted on Reddit.
I was a newish DM tackling CoS a few months ago... and it was a challenge. Two recommendations:
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Look at d20play's playthroughs on youtube. They are mostly oldschool players in 5e CoS, so it's brief compared to many but they hit just about everything. It'll be the quickest "doing everything" play through you can find, I think. https://www.youtube.com/watch?v=slOMyQjLftE&list=PL3sFiRJEF28GEicpp7uhHG1427z9wOelC
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Consider getting the first edition PDF... module I6: Ravenloft (1983) ... drivethruRPG or however. It sums up what Strahd is really about. 5e adds a ton, and I mean a ton, of NPCs. Plus 5e felt way too modern, not like an ancient world from 1000 years ago. And 5e mixes up a lot of non-vampire/non-wolf stuff into it... which might be good or might start to feel non-Barovia. It was too much for me, so I cut 90% of the NPCs out and just made up my own side adventures. To each his own there. Even "Bob Worldbuilder" admitted recently he did the same thing, went with the 1e version of Strahd b/c the 300 page 5e version was just too overwhelming to ever start.
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If you want to do "most" of the 5e content... I'll tell you what I recommend/what we have done. Many people say Deathhouse is too hard or whatever (it sounded fun to me, except at level 1 would have been too hard at the boss fight. The party at my table was already level 5 so we skipped it). Do the town of Barovia (all the main characters there), do Vallaki, but cut out as many NPCs as you don't feel like dealing with (mayor election fights in Vallaki and festivals and whatnot was not our style whatsoever, yikes). Cut out the werewolf den on the west side. Do the DragnaCarta's Bluewater Inn scene with Strahd coming and being a menace (that fan version is written very very well): https://drive.google.com/file/d/1MEm_VpOd7_8Ev0xyjGwnWgdAVDAYkX_0/view Do the vampires in the coffinshop in Vallaki. Do the evil Druid area in the west (big Strahd shows up) and the Vineyard (and the wereravens, though we slimmed the wereraven family stuff down a lot). Probably do the 3 nighthags, but make sure your party is leveled correctly. Do the Amber Temple (last probably should be level 8 or 9, and bring the duskelf guy, Kasimir Velikov, as a helper NPC party sidekick), but be very careful that you don't let your party TPK in that first giant room... read up on the Arcanaloth and the flameskulls, and make sure the players can have a fighting chance. Amber temple is were we are still... almost finished with the Amber Temple, and after one more stop we'll go to Strahd's castle and hopefully the party will finish this evil vamp off!
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Oh, and study up big time on the DarkGifts in the Amber Temple. They can be too much/change the whole course of the game if you just go by the book. Recommend only allow one per partymember or maybe none if they don't want to be grotesque, and warn them what will happen (black oily hair grows on character's face and body... forever... type stuff and worse, so they will hate their character after... so many people on Reddit say don't warn them, I think that's awful to do to your players, but that's me). Also the Sheild Guardian in the Amber Temple is probably WAY too powerful... you might want to talk to the party and say "hey, do you mind having a super NPC that will be way better than your real characters? If so, how about it only lasts till we leave the Amber Temple then it stops working", or something like that. Our party decided they will donate the Shield Guardian to a town in Barovia that needs it for protection... nice gesture.
More Vallaki tips if you want to do more there: https://www.reddit.com/r/CurseofStrahd/comments/jkd6o7/how_to_prep_vallaki_in_one_hour_or_less/
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