Oo, rooftops are good - traversal complications. Had sewers in my head as pending (gotta do some gross stuff like fatberg elementals), good call.
Don't really need an Environment for every possibility, just containers to hold some Actions that I can grab (eg: Streets suburban or urban can have something around The Lights Go Out, Suspicious Passersby, Do Not Cross, etc).
Should note this is specifically Seattle, and very high but hidden magic (as suits Daggerheart). Touchstones are entirely books (I don't really watch TV): the Matthew Swift series; Alex Verus series; October Daye series; Twenty Palaces series; and Rivers of London.