You're absolutely right.

Raising at a specific location is mature technology; the pole is controlled via an actuator, and rotated with a controlling drive. The final contacting is made with guide boards, normally around 1.5 m long, and set up in an inverse Y shape. The shoe may have to be a bit longer than it used to be, so that it will get guided properly to the wire.

As said, that happens hundreds of times, every hour. Very often at a regular stop, or at a traffic light. The whole thing takes maybe 15 seconds.

FWIW, I have seen installations where no retractor was installed; lowering and raising was all done with the actuators.