[Kako]
I've added another question, though this one is optional: What skill level would you suggest entering the Alley at? Can you give some examples?
depends on how money desperate you are.
If you are going to a local convension with low tabling fee and low admission charge, then you can go try regardless of your skill, and at least have fun and meet other artists.
If money is a big concern, then you better either be at pro level, or pretty good with chibi fan art.
When it comes to make money, it doesn't rely on skill alone. Some times having a distinct style helps, but sometimes having a generic popular anime style helps too. Sometimes being original sells, sometimes fan art sells. There are people with similar or even a little less skilled than me, but they manage to sell more than me because they either have more fan art in their showcase, or they have more appealing style to the public.
Can't say what level to suggest. But if it helps, here's my con stats: I've been to 5 cons so far, and only made money in one of them, losing money in the rest (around $100 to $200). Those include con cost, table cost, transportation cost, and hotel cost. Most of my money lost was due to high air line price. So if you aren't sure how well you'd sell, go to a nearby con.