Update: I found a workaround to fix the issue. Another year passed, and I had the same problem again, but noticed it's only affecting the resolutions that have to do with aspiration milestones. If you change aspirations and THEN hit a milestone, you will get your resolution finished. I know that may be annoying, but it did work fo rme.
NONE of the resolutions are working for me now. ><
It might be related to the 'whims not fulfilling' bug, thinking about it.
@crinrictI just did a me too on this bug because I got it twice in the same family, and I can confirm its not just the asperation resolution.
Travis Scott and Audrey Scott both are working on the Successful Linage Asperation. They just needed have a child Earn an A in High School goal to complete the milestone and made that a resolution for the year. Clair their daughter, in high school had a B grade and made it to A on Wednesday, she also had a Resolution of Become a Better student, this resolution should have cleared along with the complete a asperation milestone, but it did not clear on any of the sims that are affected.
So when Clair went from Grade B to Grade A, this triggered the Asperation to complete the last goal of the third level in family linage have a child get an "A" in High School, this should have triggered the Resolutions to complete the asperation milestone for both Scott and Audrey, the A in high school should have also triggered the completion of the resolution of becoming a better student as she went from grade "B" to "A".
Edit: I can confirm the resolutions are still broken after 9/17/2019 because the patch notes said nothing about fixing it, another thing I just ran into the bug after the 9/17/2019 during my round of playing it.
Edit2: I have found a work around for the asperation milestone resolution not completing with Successful Linage asperation in step 3 when all goals are completed except for the have a child sim get an A in high school, change the asperation to a different asperation so the asperation don't try to complete when the sim is coming home from school, the popup Claire would like to invite from school over ok or cancel this breaks the asperation from sending a asperation complete message, which prevents the resolution from completing, by changing the asperation to a different one until after the school events are done and that child has completed the goal, when you click on adult sim go back to same asperation again the asperation will say milestone complete, and the resolution completion will be triggered.
Note: I just found a work around for only one asperation with the problem.
