I also had this happen recently and have never noticed completing an aspiration milestone not counting before for New Year's resolutions. I've not tried a factory reset recently but have no mods/cc in my game, always delete my localthumbcache and repair my game very frequently. My sim completed at least two aspiration tiers and neither counted. I have all the packs available as of now (Jul 2019) and my game version is PC 1.52.100.1020 (ie the most recent update). Here's a screenshot just as she completed and before it went to the next tier 
Here's where it's showing as not completing it (the second screenshot is after the first one 🙂 ):
Thanks and regards,
Jennifer
Just reporting in to say I did a factory reset of my game before playing this household again and my sim completed at least two more tiers of different aspirations and neither counted. Neither aspiration was her original aspiration, but it's always worked for any aspiration milestone in the past for me.
Thanks and regards,
Jennifer
