For example:
Q1: What are the advantages of hiring a contract PM over using an in-house staffer?
Q2: What are the advantages of using an in-house staff PM over hiring a contractor?
Would such a pair of associated questions be accepted? (and a different question - would they be too subjective?)
I think what Jeff Atwood was alluding to in his comment is that the best questions are the ones that involve a real, actual problem that you are facing. What makes these types of questions so special is that the problem is unique to your situation, yet will also add value for other visitors of the site who may be facing a similar problem.
Questions that are contrived tend to be more generic and more like something one would expect to see in a textbook. Additionally, the responses to those questions will likely be short, textbook-style answers with little value to experts or people who have spent a significant amount of time in project management. What really adds value to the Stack Exchange network is the individuality and experience that we see in the questions and answers. That's what makes really great content.
Furthermore, when you ask great questions, you also elicit great answers. Many expert project managers and enthusiasts will have experienced a problem similar to yours, and their shared experiences will add more value to the site than something we can find in a textbook, a manual, or the front-page of Google.
If at all possible, I encourage you to ask your question and include the problem you're facing. Give us the details, and we'll provide great answers that will not only help you, but also it will help this site meet it's goals of becoming great!
What I would expect to see in a situation like this, as with anything that has more than one answer, is two opposing answers both get a lot of upvotes.
To give a simple, trolling example, if someone asked on StackOverflow "Is Java better than C#?" I would expect to see two answers with similar upvotes: "Yes" and "No."
