From someone that is from Indianapolis and loves the city, you will have to be ultra careful when choosing your con date. We are sorta packed with conventions anymore. As much as I LOVE having it in my backyard, it may not be the brightest idea. It falls right after GenCON and right before several Toy fairs if I am correct. Not 100 percent sure on that. Also keep in mind massive sporting events as well. Basketball, football and baseball stadiums as well as the Motor speedway all right down town. Chicago in't far for me, nor is Ohio. I could do either and I know that Colombus already has a fairly substantiall MLP following from hosting TROTcon every year if you are hoping to snag some newbies. Just saying.
Actually I'm gonna toss LOUISIVILLY, KY into the ring. They actually have an amusement park in the middle of the city as well as HORSE RACING and a ton of horse themed stuff not far from the city itself. The hotel a friend and I stayed at was only 90 for the night for a suite for a queen and a pullout couch. Its also had a full kitchen. It has a lot of potential. So many horseracing themed ideas for the fair its not even funny.