i would do what you want by creating an associative line at your desired point on the cyl. you will need a tangent datum to make an associative intersection line:
you can create a datum plane tangent to the cyl face by:
create a first datum pl (DP1) thru the cylinder center by clicking the cyl face. then create the tangent datum pl (DP2) by clicking the cyl face, then DP1. use the alternate soln (1-2-3) button to go to quad pt u want. if you need a DP tangent at a non-90 deg angle, create a third plane by clicking on a datum axis thru the center, then DP2, then input an angle.
create the "silhouette" line by using insert - curve op - Intersect. turn on asoociative output. pick the datum plane as "fist set" and then the cyl face as the 'second set".
you can now create a sketch and add geo constraints back to the associative intersection curve.
-rich