I'm pretty sure both words have to match the grammar of the rest of the sentence. I think the sentences you wrote simply can't be written in the form you're trying for. Furthermore, doing that unnecessarily complicates the sentence and annoys the reader by making him/her do extra work to get your message.
Are/will the Chicago Blackhawks be a hockey dynasty?"
Are the Chicago Blackhawks a hockey dynasty? Will they ever be (one)?
The official(s) coordinate the game."
The officials coordinate the games. (It seems highly unlikely that a single official could do all of the coordination alone.)
When you do use the word "or," though, remember that it's dysjunctive, the opposite of "and."
Tom and Bob work.
Tom or Bob works. (The second noun controls the grammar.)