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Oh that's tough. Do you feel like you could pull each of those things together if you tackled them one by one, and at least put some estimates on things, even if you point out that they are estimates?
I would pull together all your thoughts/make a list of tasks etc and try to map backwards how you would do something if you were dropped into it today. What kinds of things would you need to know to do the job the way that you would do it? What predictions could you make? Are there any estimates you can make based on things in the past? Basically just think it out in your mind, if this happened, then this would probably happen and we'd need these people to do this etc. What results do you want to see to know that something is successful? Might be a good exercise in general to realize that you're actually more put together than you think, it's just all in your head and not on paper. Map it out and then turn it into something that makes sense to him. Not sure what you mean in regards to the product road map - do you have one to work off of that would be valuable?