Any thoughts on how I would I achieve these clumped and layered fly-aways on the sides of my hair reference (red). Also this clumping and stray hairs mix (blue). Everything always looks either too clumped/neat or too frazzled. It's more like a layer of stray hairs on top of clumping. Lastly, curling. How do I get the hair to curl (just a bit). Using the kink settings doesn't really seem to produce usable results...
Asked and answered in Discord....I referred to an older course by Kent Tramell: https://cgcookie.mavenseed.com/courses/styling-and-shading-realistic-hair
It's about long hair, but dives into making several layers of hair, that can be used in this case as well I think.
Dangs your model is looking very realistic, there is something in the expression being relaxed that feels very life like. As Spikey said, I think that course can help you achieve your hair goal. From what I can tell you need a more manual approach and less fiddling with the settings.
Also your real life picture is too awesome, straight out of a lord of the rings character. I bet Gandalf would be like, Thorin, I got an extra companion for you, off you go Bilbo.