User Testing for Long Term Use

I have a usability test coming up and I want to test to see if one user journey performs better than the other.

It's for a task that you could do daily, ie; setting up calendar/reminder.

Essentially it's about power users vs casual users. One user journey is clearly simpler and would probably perform better doing the task once, but is a few more clicks.

However, you know how a task can become slightly cumbersome, and those additional clicks starts to annoy you a few months down the track. How do you test for something like that? It's not like I can ask this user to perform this task replicating 3 months worth of use in a 1hr session. I can ask the user to perform this task multiple times, but is that enough?

Thanks.