I have just bought a Nuvi 2559LMT and am using it with Basecamp 4.4.7
My problem is that every time I send My Collection to the device, it duplicates both the routes and the waypoints on the device. Also if the same waypoint is used in more than one route, then that waypoint also is duplicated. In some cases I have ended up with the same waypoint 6 times as a result of having a route ending in a place where another route starts and where I have updated the device more than once.
The obvious workaround is to delete everything from the device before updating it from Basecamp but that gets pretty annoying after a while.
Anyone had this problem and found a better solution?