@SimGuruNick
Here is link to my save file: https://1drv.ms/u/s!AsZLFY7em2gr3j8frVAU57GkXPl4?e=iVeFTt File name is dolldrms1FreelancerNoTaskCheck.rar I have included the .save file and the Ver0 file as well, since I think you'll have to roll back to it to see the issue.
When you load the .save go to Claire Charming hh in Brindleton Bay. She will be at Quad Manor library in Windenburg. I had her paint the portrait at home on the sketchpad and travel to the library to study the reference images. She did the study and the task did not complete. However, if you simply have her do it again, it will be checked off because I had saved and exited the game after the task wouldn't complete after traveling to the library and she won't have traveled when you first load her.
If you roll back to the Ver0, you may be in the Jolina hh so just travel to Charming in Brindleton Bay. Save and exit as I did after doing so. When you reload, to follow same steps I did, paint portrait at home, travel to library to study images = task won't check off as completed. If you then save and completely exit the game, reload and tell her to do it again, task will check off.
There is also a last exception file included in the .rar. I have no idea why it generated. Before I had her travel to the library she hadn't left her lot but a random, unknown sim had just walked into the hh, looked like to scold my sim's dog. I couldn't get an option to appear to ask her to leave after an introduction so I ended up just traveling to the library leaving the sim in the house. Perhaps that's why the LE? Don't know, it looks like an LE I've seen several times since installing the 1.55 patch and I have no clue why it's occurring.