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Can you try simulation now? How does it work?
This is strange. You mean that the route does not show following the road? Are you sure that you have loaded the City Navigator map onto your GPS? Remember that you need to transfer the maps from your computer to the GPS using Map Install.
Is it still giving you trouble?
Try using the files that I created just to be sure (all files will be there temporarily for 2–3 months after this post):
Use this file that I created using BaseCamp. Does it behave the same?
How about using the one I created using Ride with GPS?
Once you have the routes on your Mac, drag & drop onto BaseCamp. In BaseCamp, create a new list and put all of them in it. That will make it easiest to export them.
Put all the waypoints that you want to use in a new list under My Collection. From there, export that list into a GPX file and copy it to the unit. Or transfer it directly from BaseCamp to the unit.