Base Camp is frustrating in the beginning, very much so but has a huge learning curve one you start to figure it out. Read the tutorials, they help. Make a start point and an end point, use the pencil you talk about to choose your shaping points in between, you do know you click on the route first and then drag it over to the new point right? Know how to "go back" and how to use the eraser. Use intersections to click on and it will be shaping points rather than way points and then they will not alert. Alert can be turned off in the list that was mentioned if you end up with one. I see no reason to build it in Google or HD first then convert just learn to use Base Camp. Turn all the restrictions off like "avoid interstates" or "choose curvy roads" and just go with "fastest time". Get someone you can call you when you have a question, that is a huge help. Good luck but that route sounds like a big job for a beginning Road Captain.