I tested the issue in a new save file and made two separate households with different active careers. I found that both the reaper and acting careers work; I get the pop-up message/can join them at work.
I know my Sim in the screenshots I attached doesn't work from home. She also owns a business (with the Businesses and Hobbies pack). As for the amount of Sims in this household, I have 8 Sims - her, two children, one toddler, one newborn, two cats, and a horse.
On the same save file, I have a couple of Sims in a separate household who are both in the acting career. The issue also happens with them, and none of them own a business or work from home. It's also just them two in the household - no other Sims. This problem happens with all of my Sims in active careers.
So I think it's an old save file issue. I also had no issues with this before until the recent background update or whatever it was. The other day, I got a Sims Delivery pop-up asking me to download something.
I can't test the doctor, detective, or those careers because I don't have Get to Work, so I don't know if those are buggy, too.
I just don't want to start all over and use a new save file to bypass this issue because I have lots of hours put into this save. This is also the only save file I have; I have no other saves (not counting the one I made to test this bug).
If I'm able to, I can attach a video to better show what happens with this issue. I'll add it when I get the chance.