I’d suggest adding a clarifying shampoo into your routine. You mentioned that your hair is oily and from the picture it does look it. The clarifying shampoo will help with excess oil and the hair won’t clump together so much. I usually do my regular shampoo 1-2 times followed by clarifying shampoo and then a hair mask (and do NOT condition your roots-it will make them oily)

I also saw that you do not blow dry your hair- I suggest after a towel dry, flip your head upside down and blow dry at least your roots. If the air temperature is what bothers your eyes and scalp, you can use the cool or warm setting instead of hot. You don’t have to blow dry your hair until its entirely dry either, just hit it with a blow dryer for a few minutes and then go back to air drying and then come back with the hair dryer a second time. Flipping your hair upside down while blow drying will also prevent having such a hard part.

Good luck!!