Questions you'd be crazy not to ask at the start of your next project

I agree with your checklist point. I've witnessed smart, creative people abandon thought and agility to complete a checklist. I've personally struggled with this issue in our business development process. When we're meeting with a new client, I get so excited about their project, that I dive into technical details and forget to ask fundamental questions about milestones, schedule, resources, etc. But when I have a checklist in front of me to ensure I ask these questions, I'm too focused on the list and miss important details specific to the project. We've found that a decent compromise is to have at least two people from our side at every meeting. One is dedicated to scenario-specific quick thinking and the other more mechanically ensures we've covered the fundamentals. It's still not perfect for some of the other reasons you mention, but having only one person in charge of the checklist and having others be checklist-free seems to allow for a good mix of agility while ensuring the critical parts of our process are followed.