I do a similar setup during my DMing, except that I use maptools (
http://www.rptools.net/?page=maptool) to provide the interactive mapping with tokens, sightlines, etc. Then I just embed the link to the map within the encounter to start it. Not to add another app to your mix, but RW isn't a VTT. Programs like maptools or other VTT items might be more useful for what you're seeking mapwise.