I don't know how useful these questions are. Surely, every single one of these questions can be answered with "I don't know but I have faith" which is exactly the reason why religion survives and thrives. These questions only work once the wall of faith is vulnerable.
Having said that, an impressive list of insightful questions indeed.
I agree with z10 on this one. Those questions fall on deaf ears if they are underpinned by faith. It's that foundational stone that needs to be dislodged, which will make the above questions superfluous (for me anway). So here are a couple of questions that I would ask.
1 - Am I absolutely certain that Islam is true? Bearing in my that there are hundreds of religions from which to choose. What criterion am I using to make that judgement? What if that criterion is empty and not legitimate?
2 - Is it because I believe in God that I follow Islam, or is it because I trust Muhammad? If it's the latter, how do I know?