Am I doing this wrong (haircare)

So I am prone to hairfall. My iron levels are turbulent and I have an auto immune disease that causes inflammation and I tend to go through phases where I just shed like a Husky.

Anyway, I am trying to be more gentle on my hair but no matter what I do, I just seem to be pulling out more hair than I'm growing.

I am trying to do head massages and oils and hair masks and no matter how gentle I apply, my hands are COVERED in hair afterwards. I don't apply in a rough manner, I don't move my fingers up and down, I do small circular motions, I don't apply too much pressure... I just can't stop the hair from falling when I do ANYTHING. I also only do this twice a week max.

Does anyone else have this problem, am I doing something wrong?

Thanks in advance.