Yes, all regular octagons are similar. All regular x-gons are similar, as long as the x is constant, as they must have the same angle measures to be regular.
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Assuming regular octagons, squares.
They may have no lines of symmetry or they may have some - it all depends upon the shape of the irregular octagon. Only regular octagons have 8 lines of symmetry.
-- All regular (equilateral) triangles are similar. -- All squares are similar. -- All pentagons are similar. -- All hexagons are similar. . . . etc. Any regular polygon is similar to all other regular polygons with the same number of sides.
No it does not tessellate you have to pentagons in order for it to tessellate. * * * * * It is not at all clear what "have to pentagons" has to do with this. No polygon with 7 or more sides will tessellate. Octagons will tessellate if mixed with squares but that is not "proper" tessellation since it involved more than one shape.
There are 64 sides in eight octagons.