So here is one thing I've found that seems to be avoiding the milestone bug so far. Played for a couple days like this without issue (or there is something I haven't noticed). Leads me to think milestones have issues being loaded properly depending on the method of load.
- Before rotating families, make a new save. Edit: Make the save under a new name. I wouldn't overwrite any saves with the current bug so you always have a backup.
- Exit to main menu.
- Click "Load", NOT "RESUME" to load that save.
- Select the family you want to play.
Follow the above steps every time you want to rotate.
Why not "Resume"? Doing this takes you directly into the family you were already playing which means you have to go through "Manage Worlds" to rotate families. Using "Load" takes you directly to the world view instead of dropping you straight into a household.
I have done a couple rotations between two families this way over a few hours of play time and not once did the bug occur, even when traveling to other lots. Feeling bold enough to try taking control of a third family and see if this continues to work.
Just note that I have not tried merging or splitting households yet so I'm unsure what will happen in that scenario. I would say stick to using the "Load" button and always check the milestones of your Sims when you first load in so you don't invest any play time into a broken save.
Hopefully this will work for others and let people enjoy the pack while waiting for an official fix.