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To the OP, I highly recommend you go over to the Zumo forums, they have some pretty good tutorials.
With that said, I do agree that it is a big pain. Not intuitive at all. I now use HD Ride Planner because I can share it with my buddies. I have friends who ride BMWs and Goldwings, and the Ride Planner makes it easy for us to plan a weekend ride. We can post the ride and then make suggestions before agreeing on the final itinerary.
When I plan multiple day trips, I break them down into Day 1, Day 2, etc. That way if I decide to change my route I can do so, then pick it back up when I get to the next waypoint, and it makes it easier to edit when I'm on the road.
In settings you can tell it to avoid highways. I use that a lot instead of planning a route ahead of time. I can just enter the destination and it keeps me on the back roads. Very nice feature. Routing on the other hand allows you to plan a trip which includes stops and roads that you want to travel along that aren't necessarily between your starting point and your ending point. It allows you to travel a "roundabout" way. So using the setting "avoid highways" and routing are useful at various times.
I like to get myself lost during my outbound ride, and then while using the "avoid highways" setting, set my destination as my home when it's time to start moseying back home for the day. That way I'm traveling back towards my house but staying on back roads knowing I won't find myself going too far astray or getting into a dead end situation. And not having to spend too much time backtracking.
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