I am sure someone will point it out that there is a thread already, so here you go, a link to the former thread here, as that thread was going to end up becoming irrelevant to the new update I am posting now. If you are curious about the former discussions or the previous versions of the guide to see how much has actually been revised and changed and the discussions had, I suggest checking the thread out.
Now, to cover some basics. This is not finished. This is still missing huge parts of the guide, such as the new backgrounds that I am working on, though the names are present, madness effects, curses, altered magics, equipment, and creature rule updates. I am well aware of this but when people see how many pages this new update is currently at I hope many will see how much work I am putting in and understand why it's taking some time 
As with the previous guide, this is a labor of love, and I am doing my best to pay respects to all past editions writers and artists that worked on this campaign series, and I make no claims to any of the work. Not all art is in, but all art, to the best of my knowledge, comes from an official Ravenloft or DnD product source and as such is property of Wizards and their respective artists. Even with the expanded and more example based writing, it is still expected that players have owned past editions of Ravenloft to utilize this conversion guide completely.
I am hoping for feedback on this as I took a lot of what I saw from the previous thread and looked over other things to hopefully streamline and improve upon what had been previously written. I hope what I am creating is paying the respects that the Ravenloft campaign deserves, and maybe can help convince Wizards that Ravenloft is still alive and well and deserving of a new chance.
Unofficial Ravenloft Conversion Guide <--- Click link for PDF
I just noticed that I forgot to put int he stat that madness checks use. This is a charisma check, something some my know if you've read the previous guides. The reason for this is that As you attempt to wrestle with your mind and wrold unravelng before you, you are trying to console yourself, convince yourself of why something is happening or at the very least there is a logical reason for it. When I update this update, that will be in there properly, as well as the rest of the madness check rules.
Have you considered making Gypsy a Rogue Archetype instead of a background? The original Gypsy class was essentially a Rogue that could cast Divination spells and specialized in knife fighting. I think it would be better balanced to make an archetype somewhat similar to Arcane Trickster (spell casting rogue) than to try to balance a background that grants spell casting. Just a thought.
I'm headed to work in a minute, so I only had a chance to briefly peruse it, but overall it looks pretty great so far. I did notice that Tiefling was misspelled, though.
On a side note, I've been converting Strahd as well, and my version had him as a level 5 Eldritch Knight (Fighter)/Necromancer 15. I thought that the Eldritch Knight fit closely with the description of Strahd in the novels, as he was a fighter that was dabbling in magic before making the full switch over to Necromancer. The advantage of making him an Eldritch Knight gives him a few extra spells, allows him to two weapons bonded to him, and 5th level gives him an extra attack. Aside from the Ability Score Improvement, there is virtually no difference between a 15th and 16th level Necromancer, so it's just a matter of preference between increasing his stats or giving him an extra attack. However, I think Strahd is a character that's totally open to interpreting him several different ways, so there's certainly no WRONG way to convert him. I just thought I'd mention that particular build.
Thanks for all the great work!
Just what jumped out at me
Pg 3. You might want to add a line about the product not being endorsed by WotC. Check out the requirements of their Fan Site Kit for what they want in a disclaimer.
Pg 8. Ghouls have always been intelligent. They're free willed, just derranged. Like feral Forest Gumps. And they're regularly described as "cunning", likely using ambush tactics and the like. Ghasts are as intelligent as any human.
Unexpected spells that are Necromancy: astral projection, clone, eyebite, false life, feign death, raise dead, ray of enfeeblement, ray of sickness, ressurection, spare the dying, true ressurection. Should someone potentially become a dark lord for casting false life?
Pg 12. I've considered making drow the elven equivalent of caliban. Thoughts?
Pg 21. Couage/Jaded/Open Minded. Proficiency on checks? Are these skills now or three brand new saves? If you already have proficiency to the saving throw, do you add it twice?
What are the actual mechanical benefits of Ghostsight?
Pg 22. Hypnosis. No other skill cannot be used without proficiency. That suggests this should be part of a feat or something.
Backgrounds are what the PC did before they became and adventurer. They're what they did in their early life, their backstory. I'm not sure if Monster Hunter or Kight of the Shadows are great examples.
Pg 23. Page 174 in the PHB has a list of typical DCs. Your chart could mirror that. The DCs on your table seem to increase randomly, going up by 3, 2, 5, 3.
I like the inclusion of the conditional modifiers sidebar.
I'm not sure why bringing back the three stages of fear from 3e is necassary. The fear rules changed to accomodate those rules in 3e, and should change to accomodate the single frightened condition in 5e. If multiple stages of fear are completely necassary, you might want to consider levels of fear, like how exhaustion is handled in 5e.
Pg 26. As "shaken" and "fear effect" are not generic conditions, Aversion and Fearstruck should describe the full effect, Frozen is pretty much the Stunned condition. To keep in line with the language of 5e, it should be phrased something like "The creature is overwhelmed by the scene and is stunned for 3 rounds. At the end of each of its turns, the creature can make a DC 11 Wisdom saving throw. On a success, the effect ends." (It's always a good idea to see how the book phrases rules and try and emulate that style.)
Nausea. What's a "partial action"? And the text should probably read something like "The creature must succeed on a DC 11 Constitution saving throw or its hit point maximum is reduced by 1d6."
OrdoVeth23 wrote:
The_Jester wrote:
Ravenspyre wrote:
The_Jester wrote:
Anyways, further thoughts, on the whole free-willed argument, this is how it will be defined; a creature is created or another more powerful creature can assume control and direct what it can do (through powers and natural abilities not skill rolls or magic), then they are not considered free will, even if their behavior without such control might dicate otherwise.
On the thought of the backgrounds, I am considering this instead, taking a variant of your Dark Shadows, but considering this background expansion, as it were. Basically a player takes their normal backgrounds, per their usual stuff. Then these optional backgrounds they take to repesent further character development in their life. If they take one of these optional backgrounds then the rules that are provided would overlay with their original background, and may supercede them. I will try to have a new version of my guide up by Wednesday so I can hopefully have examples of what I am talking about to present. I also plan on putting in at least the Madness stuff and maybe a bit of the Curse stuff and at least the Vampire section so as to at least hopefulyl explain why Strahd has the stats he does.
Ravenspyre wrote:
I am going to probably take a few more days to work ont he next iteration of my update, so it probably won't be ready by today. A few things that will undoubtedly change though in this iteration, and after considering points made;
- The fear and horror checks will probably have a base 11 DC with the ranges being 11, 13, 15, 18 and 21 to be a bit more consistent.
- Backgrounds are still in the air. Probably a few will be lost in the end.
- Updating some of the feats to be more consistent with those presented in the 5th Edition handbook, thus things like Courage may see actual ability score increases as well as a few other features.
- Double checking additional feats and seeing if they can be added as well.
- Finish up the Madness section. Altered magics will at best be an overview of each of the schools and explanations of changes. It will be up to DMs to decide what spells are vastly different.
- Exapanding the Secrets of the Mists sections with altered monster data, refinements to Strahd's entry and better clarification on Domain Lords Legendary Creature status and Lair benefits.
- Possible guide to creating a domain for DMs who wish to create their own domains that fit their campaign needs.
- A lot of spell checking and gramar fixing.
Ravenspyre wrote: