Hi @elesliemeehan! Welcome to the community!
You make some really great points in your post. As a developer myself, I understand the challenges of having the necessary information to provide accurate estimates. We have a number WordPress Pros that have been able to succeed with the information we collect today. I believe the key is to let your customer know that the estimate you are providing may change once you connect and get more information.
It comes down to cost/benefit when we require information on the WordPress Request form. The more information we require, the lower our conversion rate is, the higher our cost per acquisition (CPA) is, and the more we have to charge our Pros to compensate. With that being said, I believe we may be able to add a question or two to the request form without greatly affecting our conversion rate.
As @Erica pointed out, we do have an official Feedback Forum but if you were to add just 1 or 2 multiple choice questions the form, what would you like to see? I cannot guarantee we will add them, but I promise I will consider your ideas. 