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So how do I go about creating a terrain map in Unity with contours?

I use the terrain.party website to create height maps of real world locations. Once the height maps are downloaded, you'll need to use Photoshop or Gimp or similar to convert them to .raw format, so that Unity can read them. Once you have the height map in .raw format, you can create a terrain object in Unity and apply the height map to displace the geometry. I'll leave it to you to play with the settings etc. to get the effect you are looking for, but this should get you started...

I have been (and still am) in a very similar situation, and I suggest that you avoid being "subversive" - I get the impression from your post that your boss likes to have his fingers in all the pies - so if he feels you are undermining him or taking your own path on this, he will move to block you, and you will find the whole experience even more frustrating. If you can, find someone who has the boss's trust, convince them of the merits of your approach and the reasoning behind it, and use their support to convince the boss to allow you the leeway to get moving. Once your champion is on board, pull together a small team, which includes this person, you, the designer, and at least one representative from the end users (you can change the representative(s) at different phases of the project). Start with the designer's layout, and start chopping it into discrete functions - as others have suggested, it's best to take an educator's role on this and let the users and the designer figure out the bulk of the issues, while you take notes, provide technical guidance and ask leading questions, when appropriate. Most of all, provide the boss with regular summaries of progress, without too much detail, and at the same time without being evasive. Good luck!!