I've carried this topic over from the next year in St. Louis thread.
A. Hotel: When booking a hotel you want your negotiation skills sharpened to top notch razor sharp skills. You'll be signing a contract so it's always good to check things over before actually signing it. You want to use the words 'sliding rate' and if you want any sort of deal on the conference rooms you should set aside at least 100 rooms for attendees. Mind you, you don't have to pay for these, ever; the hotel will let whatever hasn't been filled loose about a week or so before the con for the open public.
The sliding rate pretty much means that if you can fill the block you get a metric crapload off of your con space (sometimes free). The hotel will do this because you are filling their hotel with guests, they'll supply the fun rooms.
Also make sure you know what you want to do about food and any AV equipment before negotiating with the hotel. Many hotels are VERY anal about outside food in con space (not hotel rooms but actual con space) typically hotels have outside contracts with companies like Aramark which mean that they have exclusive rights to any catering type things that go on. They're ALWAYS expensive (monopolies are) and if you can find loopholes there more power to ya.
Same with AV, some hotels allow outside rentals and equipment but many will ask you use theirs. The theory has something to do with insurance reasons, but I think some of this is also so the hotel can make an extra buck... which is fine, if you're filling the rooms they're giving you space.
The hotel should be easily accessible from the closet major airport and should offer free shuttle service to and from the airport (most do)
Make sure you have a good idea of what kind of space you need as well. Hotels will find lots of ways to charge you for things you wouldn't think you'd be charged for, like excessive use of electrical outlets and phone lines (if you want a dealer's room they're gonna want phone lines for their credit card machines) Hotel negotiations are frequently overlooked but are vital if you want to make sure the con has any money for anything.
B. Timing- Timing is key, even though this is a unique web comic con I would advise not competing with any anime or comic cons if at all possible. Especially the heavy hitters. Many webcomicers and web comic readers are pan-geeky. You don't want to make them choose between the con they go to every year and this new one, because you'll loose every time.
While there is hardly a weekend anymore where there is no convention going on you should be careful. St. Lois in early June is tough, it ain't too far from Dallas which already has a very popular A-Kon typically in the first couple of weeks of June. Actually, summer is very con-heavy and putting the con in the summer is risky (not deadly, but risky)
C. GoH- Guests of honor are fun. This is my particular area of expertise as there hasn't been a con I've worked where I wasn't at least on Guest Relations staff (but frequently heading the department). You want to book them 6 months in advance if at all possible. This will allow them to have you as a priority on their schedule (few people have anything planned out 6 months) Instead of them having to bump things for you, they'll have to bump you for other things. Most people will honor an agreement made ahead of time.
Always pay for travel and accommodations for GoH. ALWAYS. Some will ask for an appearance stipend, unless it's someone BIG (I mean HUGE) I would advise against it. Some guests will ask for space in vendors or dealers room. This is acceptable. A full dealer’s room always looks good and first year cons always have a thought time filling them. (a lot of vendors want to know about demographics before saying yes... and it's good to be honest, don't overshoot your estimation in hopes of getting vendors because if you're wrong they won't come the next year)
Guests should also be unique. While there are always fan favorites (and always get some fan favorites) I recommend also getting some people who have never guested at a con before. These people are draws because they're fresh faces. The fan faves bring in the fans, but the new guys bring in people that want something a little different.
D. Image- You want the con to be a success, in order for this to happen you need to have an image. What is the con? Is it going to be solely webcomicy? If so you should ascertain the draw for this. You'll bring in a lot of webcomicers, but how many non-webcomicers will you snag?
Personally, I think it's wise to not be too nichey (Nietzsche?). Which the con should certainly have a focus on webcomicers, I think there should be some other type guests there. As I mentioned before most webcomicers and web comic fans are pan-geeky. (Multi-Geektural?) They may come to a web comic con, but the chances are greater if there is a little more to it than that. Wrapping them into the web comic package ain't a bad idea. Get published comic book people to discuss breaking into the industry. Get voice actors to discuss voice acting (should we maybe expand this to all types of webworks like web radio dramas?) Get Jewel Staite from Firefly/Wonderfalls cuz I think she's cute....
It is important to know about the image because you are going to talk about it... alot lot, becuase of...
E. Publicity. There is a unique opportunity for publicity here as your audience are by definition internet people. Publicize this con all over the web comics, that's your target audience. If you've got webcomicers talking about this in their rants... if you've got banners up on web comics. If you make yourself a presence in individual web comic forums (but don't push the con here... let it be known who you are (via signature) but DO NOT PUSH THE CON unless asked about it. Do not show up and say you're with such and such a con, its poor taste. People will go to a con you're involved in just because they know you from the forums. 'Oh yeah, I know the guy in charge of the dealer's room there, maybe he can hook us up' or 'sure, whatsherface is running a couple panels there, se would check that shit out.' It's the theory behind a lot of networking groups and CoC's. Get involved in the community and they will come.
Three month's before the con send out some PR stuff to local papers and entertainment rags (especially local entertainment rags) something like this is unique and often they'll do something for you. PR stories are free entertainment and will bring you some at door local attendees.
Guerilla marketing is really the way to go here. You want to take a look at how much effective publicity you can do for free or next to nothing. (Can we say ad in Free Comic Day book?)
I have a metric butt-ton more to say on the subject (as I have mentioned it is my area of expertise) but will hold off for right now.