Word and PowerPoint Master Doc / Template creation

General information for the business: we are consultants in health care
Industry: Healthcare
Description of consulting work: We conduct onsite consulting projects, beginning with questions and observations, which fall into categories, then we have problem statements that describe deficiencies observed (all prewritten). We need the content organized in a template to allow the team of consultants to chose from a long list of question that will result in auto creation of a form report-out in PowerPoint and then a Word document. the content and categories and problem statements are available. The template would allow the user to select content to be added by checkbox or control-panel, and the chosen content would then show up in a predetermined location in the document or PP Template. See Specification. We work in MS Office MAC and/or PC 2016.
Extra notes: This is a rush (want to trial at a client in 2 weeks), and while much content is complete, we are still creating some generic content. We would need to have the flexibility to make minor modifications to the Template ourselves, but would want a contractor who could support further development and other similar projects, assuming this goes well. We have some beginner skills, but don't have room for a permanent "documents developer". Not sure on budget, we would need to discuss, and we assume this is not an entry level project.