I was thinking sometime in 2014, but the exact where and when depends a lot on what people would want out of such a gathering. If the goal is just gaming in the room and drinking like last time, maybe a small cheap con would be a good choice. If the goal is to get everyone together for a meal and then largely go our separate ways for entertainment, maybe a larger con would be a good idea. Etc.
As the response seems to be generally trending towards positive, what WOULD people like?
Ikasucon 2014 would be pretty easy to arrange, but it's a fairly small, young, and anime-centric convention so we might not find much to do. On the other hand, there's a really pleasant pub with good food in walking distance, and I could probably arrange some awesome con events with enough notice and interest since I'm still good friends with the owners and we've kinda got a standing invitation to be guests (especially if we're bringing in people). It's likely to be very inexpensive, which is another plus if people are flying in from all over the place. And Fort Wayne is the single most mild-mannered city I've ever stepped foot in. There are parking lots where people leave the keys in their cars in case the cars need to be moved. Seriously.
Assuming four people in a room, staying Thursday through Sunday and registering early, the cost for Ikasucon is approximately $160 per person for hotel and badge.
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If we want a wider genre and older attendees but still a smaller con, I've never actually been but I hear that MarCon is pretty good:
http://marcon.org/wordpress/ I know very little beyond that except that many of my friends attend every year, and I've heard mention of Barfleet in terms of nightlife. The epic Ohayocon gathering was at the same hotel that this convention is, and MarCon is in May 2014, so might be feasible if Actor wanted to extend his trip to attend. They also have hospitality suites available, which are more expensive, but if there will be a lot of us it might be a good idea to spring for one and split the cost so we have space to hang out. Those are currently $350/night plus tax, though, and include a bedroom and a social space. So deducting the cost of the bedroom, it's about $250 per night for the social space that would be divided among the group as a whole.
Assuming four people in a room, staying Thursday through Sunday and registering early, the cost for Marcon is also approximately $160 per person for hotel and badge. If we get a hospitality suite, it will be more. For the sake of argument, let's go with assuming $100 extra (based on ten people attending), so $260 per person.
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If we want something where there will NEVER be a lack of things to do and the nights are one big party, I'm a big fan of Dragon*Con. It is huge and expensive and booking rooms requires camping the reservation website so room captains would be absolutely necessary. Pre-registration saves everyone quite a bit of money, and if that's the con we choose, I'm gonna recommend people register THIS September. Registrations can't be cancelled, but can be transferred to the hoard of eager latecomers for a modest fee if you can't make it, so it's a fairly safe choice. Once you're in it's a blast. Gaming, burlesque shows, concerts, artists, tons of guests, epic parties, karaoke, and a ton of great panels... plus many of the events are televised over the hotel TV system with amusing shorts and bumps to space out the programming, so if we wanted to just hang in our rooms we can do that without missing the con. There's usually a pretty strong webcomic presence, too. There's a good and readily affordable metro, so if we all want to escape the convention area (which is most of downtown) to get dinner together one night, we can head out to some of the nice not-mobbed restaurants and pubs in Decatur and then go back in. Dragon*Con is pretty much an extra long weekend, too, since people arrive Thursday and leave late Monday or early Tuesday and there's con happening that whole time, so it's quite a lot of bang for the extra bucks.
Assuming four people in a room, staying Thursday through Sunday in a main host hotel and registering early, leaving late on Monday, the cost is approximately $280 per person for hotel and badge. There
are numerous much cheaper hotel options in walking distance, they're just not part of the main cluster and don't get DCTV. I always stay at the Hyatt, but the other hotels are just as good, and there's no reason we can't have some people at a host hotel and some people not, either.
Those would be my three recommendations, but it really depends on how many people are interested.
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Edited for clarity and some cost estimates.