Wizard for generating a dynamic legal document
For the longer list, you can add a content type (Structure -> Content types) and add checkbox fields for each question, where the text of the question is the value displayed by the checkbox when it is selected (the "On" value). An alternative way would be to add a Checkbox field with multiple values. I suggest this because by default, just the value of the checkbox(es) is shown on the resulting content when you save and view it.

For the list of questions, it depends on how many questions we're talking about. A slightly tedious but straightforward way is to use the Rules module along with another content type that contains the questions.

This installs itself to Configuration -> Workflow -> Rules.

For each question, you add a triggered rule that checks the response and sets the value of the other content type (let's call it Template) to whatever it should be. You could probably do this one with one rule as well. In this case, I'd set the stored values in the database for the Questions type fields such that they match or somehow contain information about the names/values of the fields in the Template content type. It would basically be a mapping of sorts, and the rule could set the value of the Template based on this.

You may also need to store a reference to the Template content corresponding to the set of questions in the Questions type. The easiest way to do this is to install References and add a Node reference field to the Template content type. Then, you can have a rule that creates a new template and associates it with the Questions content when you save a new Questions content item, for example. The other rules would then have some saved content for which to set field values (otherwise, you'd wind up creating new Template content every time or something).

These are some thoughts on this. It's not the most elegant, but it might get you started or at least on the right track.