Once I figure out the proper form for doing so, I intend to ask two questions about metonyms and professional sports. There is more than one correct answer to the question, so I'm not sure how to handle asking it. Should I ask the question, then flag my own question for the moderators? If not, what's the best way to handle this?
If you feel strongly that your questions should be community wiki, yes, go ahead and flag it for moderator attention.
Keep in mind that the use cases for community wiki have been heavily deprecated and the moderator simply might not see that it is justified.