The extrude command is measuring length in the direction of the normal. As you change the angle, the surface has to extend to match the length according to the normal direction. Compare the images below for reference.


This may help also explain why this command works when the taper angle is set to 89.999 deg and fails for 90.000 deg. At 90 degrees the distance must be 0 in the normal direction!
Instead of using the Extrude command, a better command bay be to use the Extend Surface command from the Modify drop down menu in the Sculpt environment.

If the results aren't what you had in mind, another solution is to loft to another straight sketch line. I did a copy and paste in the original sketch to get the line in just the right position. This ended up being a pretty quick solution.

I hope this information helps! Please let me know if you have any questions.
Thanks,
Nathan Chandler
Principal Specialist