Roads are meant to intersect and designating a path that crosses other roads should be legal as it can just ignore the tiles that already have roads and continue to build on through. I think the issue here is that roads are not treated as individual 1x1 segments but are clusters of segments in a line so you can select any one of them to upgrade it later. What would need to happen then is that the planned road that crosses through other roads should automatically break off into discreate segments.
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