That is probably achievable, but it would be a little easier if you're willing to redefine the Block so that at a rotation angle of 0°, it "aims" in the 0° direction [to the right] from its insertion point, like this:

[Generally, it's a good idea to define all Blocks that way.]
EDIT: Also, would the end of the Polyline that one of these Blocks is attached to ever be an arc segment rather than a line segment? It would make a difference to the method of determining the rotation angle to impose on the Block. And/or, would they ever be attached to other kinds of objects, such as Lines or Arcs or Splines or partial Ellipses?
Kent Cooper, AIA