I came to this thread looking for help, and 2 min after I put my phone down, I stumbled onto the answer!
My main character has a bunch of money, but that doesn't help with the "money earned" part of the aspiration for her grandkid.
So what I did is had the grandkid open their own business while still a part of my household, and transferred money over to the business from the household funds. That's it!
I only did that because I was going to build a business to sell some violins but as soon as I transferred the money from the household to the store the notification popped up letting me know that the grandkid had completed the aspiration!!!
