I am afraid this is not feasible due to limitations of Factorios tile engine. Only 1x1 tile edges, corners or sides are supported as fair as i know. But i encourage you to post this on the suggestions forum, because this kind of corners would make other types of terrain transitions smoother too.
A road planner? Again a great idea, you're really filling my to-do-list :D
But this sounds more like an idea for a stand allone mod. When i have a little more time, i'll try what's possible.