Everyday Outfits Photography Bug?

@SnoBoz  I tried this,and only had to take 5 photos of one and only sim; not 5 different ones. Make sure they are not already in their Everyday Outfit, since they can't change into it on the screen of clothing choices then. The option to ask them to change clothes is under social interaction Freelancer, when clicking on the sim.

CC skins and clothes and mods can interfere. I suggest you try in a new folder. Here is how:
https://sims4.crinrict.com/eng/2014/09/resetting-the-game-to-factory-settings-without-reinstalling/

Let me know if it doesn't work.

Edit: There is a bug report on the tasks in the career not registering. If this fits your issue, feel free to Me Too and describe your problem in the report thread:
https://answers.ea.com/t5/Bug-Reports/OPEN-Freelancer-Tasks-not-getting-checked/m-p/8179949

My sim had to travel to be able to reproduce the issue: the sim accepted the task, then went to a venue within the neighbourhood and took pictures af a random sim; but the number of photos taken did not change in the task panel, but were still on 0/5.