1. Have you ever worked a convention?
Attending cons and working cons are totally different worlds. Before you ever start a convention, it's best to know a bit about behind the scenes. Even if you've never been able to join a con's full level staff, most will let you volunteer. That volunteering is an invaluable experience, as it will let you at least see the way security is handled, along with the convention floor.

2. Do you have friends?
Okay, so that's a strange way to put it, but really it's the core question. Running a convention takes people... lots of people. A first year convention is going to take a core group of people dedicated to the event, plus whatever other friends they can sucker into working for it. If you can get more than one person who answers yes to question 1, that's even better.

For example, No Brand Con was started by only a handful of people, but two of us had extensive convention work experience. Beyond that, we were able to drag in every mutual aquaintance we could convince to lend a hand here or there -- most of whom ended up becoming vital members of staff.

3. Can you afford to lose the money?
This is very, very important. Many cons lose money their first year, and most of those costs have been paid out of pocket by the staff. While it's true there's a chance you'll be able to reimburse everyone... there's a good chance no one is getting their money back. Don't float a rent payment or rack up a huge credit card debt you can't afford to pay for a convention. It really isn't worth it. No Brand Con ran on an exceptionally tight budget our first year, and I actually occasionally brag about how we only lost $20. This was because whenever possible, we begged, borrowed, and stole to make things work. Everything was out of pocket, but we made it work. No Brand Con never lost money after the first year, but we didn't really start operating with proper funding until a good four years into the convention's lifespan.

4. Have you researched the Cons in your region?
It's important to know what's going on around you. Are you starting an Anime con in an area where there are currently only Sci Fi cons, or are you starting one where there are three other Anime cons in the region. What time of year are the conventions in your region? Knowing these things will help you tremendously when picking a date and when doing your early advertising. I'll go more into those topic later though. In your research you can also network with other cons' staff, and find out if anyone in their organizations can help you as well.

5. Are you connected to a fan club or University?
Existing Fan Clubs and University organizations have access to resources that may make launching an event easier. If you have an organization, you may be able to ask for some of the organizations funds to start the con. If you're connected to a University, maybe the student Union would be a cheap alternative to a hotel for your first year's location. This also helps with question number 2 as well.