The first task is usually solved by applying Minkowski difference to your map and robot. This implies you know the profile of your robot.
For the second task common approach is to use 2D Snap Rounding. You can find a lot of papers on that topic at scholar.google.com. However it may also be helpful to take a look at Ramer–Douglas–Peucker algorithm for reducing a number of points in curve. It can not help with solving your problem, but it is useful to know about its existence.
Most likely your work is connected to Motion Planning, so I highly recommend you to read Computational Geometry by Kreweld, De Berg, Overmars and Schwarzkopf. It is classic of computational geometry. There you can find a lot about visibility graphs and motion planning.