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A regular octagon cannot tile a flat surface, it needs squares as fillers. An irregular octagon can tile a flat surface alone.
Yes, but only with some polygons.
Yep. ^.^
Triangles, squares and hexagons. That is if they all have to be the same. If you use different regular polygons, you can tile a flat surface with triangles and 12-sides or with squares and 8-sides for example.
A regular polygon will tile it if its internal angle divides 360 degrees.