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Have you taken a look at the "Masque of the Red Death" material? It's set in the late Victorian period, so fits with Lovecraft, Arthur Conan Doyle, etc though obviously not with the 13-1500 tech level.
You may also be able to tap other systems like Ars Magic or Vampire Dark Ages for ideas as they've covered a lot of gothic pre-renaisance ground.
As to your specific questions
1. sounds fine, no reason why it shouldn't work
2. I've been involved in similar things, tricky to stay on track and keep the balance right. Maintaining the D&D "feel" is going to be the problem, particularly now that D&D is almost just a setting for the D20 rules.
3. Should be, but bear in mind how much Ravenloft was derivative of! :)
4. Never had any problem with episodic campaigns. Rotating DMs is more likely to cause a headache I'd have thought.
5. Core D&D isn't naturally very gritty & pulpish, again it'll come down to balancing the game and making it feel like D&D and not CoC or Ravenloft. As for paladins (and clerics) look to appropriate literature for inspiration, in particular the representation of religious groups in modern gothic horror -- Vatican black ops teams dedicated to stopping the birth of the antichrist seem to be a must in most hollywoodesque apocalypses recently :) Gritty, driven, fanatically (suicidally) driven to holding back the darkness, they'll save your soul even if they have to kill you to do so.
6. Again it's the feel of it, what is the essential "D&D"ness of it that you want to retain? Gritty/pulp/hero is comic book, again quite different to gothic horror or traditional D&D. Again it's perfectly doable, but if you want to be "recognizable D&D" it may cause problems. Timewise gritty/pulp/hero has tended to only really work from the late renaissance onwards.
My current Greyhawk game will be ending around December, so I am in the process of coming up with a new campaign to replace it. In September and October I am too busy to work on it much, so I need to get a huge head start now. Here is what I want to do:
I would like to run a dark fantasy campaign using altered published adventures, with a late medevial setting circa 1300's-1500's feel. It would be fantasy all the way, with no firearms, but lighter armor predominant, the beginnings of a medical profession (not just magical healing) with hospitals and asylums, gaols in place of castle dungeon for criminals (some in asylums too), etc. The tone would be Lovecraft, Poe, Doyle, gothic influenced. I have an "adventure path" sketched out already.
Why would lighter armor be predominant if there are no firearms? Heavy full plate armor was used well into the 1500's.
My questions:
1. I feel like I am mixing genres with the gothic horror/Cthulhu feel, but with D&D characters and action. I definitely want it to be recognizable D&D, not CoC or WoD feeling. I actually DO want my good guys to be discernibly good and bad guys discernibly bad, just not to the point that they are caricatures (which is one of the faults of Ravenloft IMO). There will be lots of Neutral alignments in positions of authority. What do you think?
I think a lot of the power figures in the actual late medieval period were actually lawful evil/neutral, so this should work just fine.
2. Has anyone done anything like this before? What were the results/player reaction?
I've run a couple of mini-games in the "pirate" era with firearms, cannon, etc. Everyone had a swashbuckling good time, but that's not really what you're looking for. Any era can be fun if the good elements of a role playing campaign are there and it sounds like your campaign would be a lot of fun.
3. Can I do it without seeming derivitive of Ravenloft?
Why worry about that? Do your own thing and if parts of it seem like a derivative of Ravenloft--who cares? Ravenloft was a blast!4. I want to be episodic due to loss of continuity through alternating DM's. What do you think about an episodic campaign, where travel from adventure to adventure is summarized out of session?
E-mail could be used...you could also host a bulletin board where your players could post their character's actions between games whenever they wanted to. I'm thinking about doing that myself.
5. I want the PC's to be recognizable good guys in a very gritty, pulpish world. For example, I plan on using Dungeon adventures like The Styes, Death of Lashimire and Tears for Twilight Hollow. I plan on giving the players some generic character types to customize, so that the PC's will fit the setting. Has anyone done this? What problems would a Paladin be in this type of game?
Paladins are pretty flexible character now. I really liked that Paladins of Greyhawk feature in the RPGA supplement to Dungeon about a year or so ago...it really showed how you could make believable paladins come from all sorts of cultures. I don't have my issues handy, I'll look it up when I get home and post it here so you'll know which # Dungeon I'm talking about.
6. While it is gritty and dark, I do not want it to feel hopeless. The...
Hmmmm....quoting your text and replying directly in it didn't work out the way I thought.
My final suggestions would be to pick up: Magical Medieval Society: Western Europe....it contains a ton of information on the late medieval period and a lot of various tables to generate manors, towns, cities, guilds, power centers, etc.
While the book is super detailed, it's a great read and I use it all the time when creating towns and settings. Paizo sells it on this site and you can probably find a lot of useful information in it--especially since you're building a new campaign from scratch.
6. While it is gritty and dark, I do not want it to feel hopeless. The PC's are a beacon of light and I want their actions to make a small difference. They would be like the jaded, but gold-hearted pulp detective type ("It was a dark and stormy night."). I also like the Batman model of hero for a game like this. The setting would be very "Gothamesque." Can this work?
One thing I've found over the years is that asking "Can this work?" with D&D is always the wrong question, because the answer is always "Yes." The real question is "Can I make this work?" :-) If you've got a fairly clear vision of what you want and what elements to include to achieve that feel, and if your players are interested in playing that kind of game, then you can do it. Tell your players what you're going for and they'll help you fill in the details.