Because of the repetitious nature of workouts, doing the same one over and over again often starting at the same spot means you get very few trophies on Strava when completing your ride as you are doing the same sections at the same wattage over and over again with little variation, very few trophies appear after you have done the workouts a few times. If workouts dropped you randomly around the course when you start them then you would be doing different segments at different speeds all the time, trophies should be appearing more often, they are a nice little motivator, for me anyway.
Just a thought anyway to change things up a little.
G