Hi Pavel :) Thank you for your reply, it's indeed a very fair question!
"Most important questions that every PM should ask" if by PM you mean Product Manager, I don't believe the questions you mentioned are the most important ones. A PM's job is to change the product for the better — to create value for the customers in a way that creates value for the business. The most critical questions a PM should ask are: "What is that customer value?" "And is it viable for the business?" Those questions are not easy to answer and require flexibility and experimentation, which is hardly compatible with answering the questions you mentioned in the long term.
I don't mean that they don't need to be answered. Once we know what should be done, we need to zoom in and answer them. This post suggests tagging the items on the Product Roadmap with that info once we know it. If needed, we could also present a Delivery Plan on the side.
But what I believe we should never do is to replace the Product Roadmap for a Delivery Plan. We'd lose an excellent opportunity to communicate the Product Strategy by over-focusing on the Delivery Tactics. Strategy first, then tactics – It's true in every game and Product Management as well.