Matt, this is great for getting a feel for this place. Here's what I think:
Obviously, the map needs more intermediary height lines.
The valley to the east should be a gentler slope rather than a trough, for instance.
The plateau appears piddly viewed from the side. We might need to enlarge it.
The extra height lines on top of the Tor (for wind temple and either citadel or beacon, depends on how much of the Tor is covered by John's city outline) were overwritten by overlaying the city. Basically, we need a detail map of the Tor.
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