Poor mommie.
I agree with Mitzi's Mom that you probably don't need to empty Samies anal glands so much. I've had dogs all my adult life and only had one that had to have its glands expressed ocassionally. Not all dogs need to have that done. Some are able to manage quite well on their own.
I would just let the warm water of her bath clean the area when you bathe her and also keep the hair in that area really short. She may even enjoy sitting in the sink in warm water for a few minutes. Take her to the groomer if you need help cutting the hair but I think it will really help her to not have the area disturbed so often. Make sure she is getting plenty of water. I'm sure you are.
I hope your baby gets better soon. Tink is sad that Samie is so miserable and sends her some hugs and good wishes.