Love the first one and the yellow beanie drawing, and about the PS to traditional thing - I have constantly heard pros say, start with the traditional then when you switch to PS, all that you need to know is the tools. but you are kind of right maybe, it might help ease into it, but I think there's also an argument that, since traditional painting doesn't multiple layers, its more challenging right?
Loving the chunky fella in profile. I tried to get back into traditional a while ago, found everything took much longer and didn't look the way I wanted it too - pretty much given up on colouring outside of photoshop for now, I like being able to quickly change things.
I tend to dip in and out of painting in PS, this probably hinders my progress a lot. I find myself drawing in sketchbooks more often than not, but I love working in PS as it gives me so much freedom to play with color. My thinking is, the more I play around in PS the better informed i'll be when it comes to working in traditional materials. The aim is to eventually progress to oils, but for now i'm dabbling with a range of acrylics and gouache and then good old pencil and paper. Here's a selection of studies in these materials.
Id highly recommend looking at the Andrew Loomis 'Head and Hands' book.(you can get a pdf of it online) but would recommend getting the book. It had helped me so much in understanding the structure of the human head, he had such a clear way of explaining his method. Secondly id try to loosen up initially, lots of loose studies will mean you'll learn more in a shorter space of time rather than drawing meticulously at this stage. The 100 head challenge is a great way of developing your portrait drawing. Go for it. These are great.
Ive been building up to eventually/ hopefully using oils. This is great. I used to live just along the road from Jackson art supplies in stoke newington. I still use them as my go to if my local art shop doesn't have what i need. I think i need to stop over thinking oils and just give them a go already. I told myself that i will get better at painting portraiture with acrylics first, but maybe i should just dive in with oils already. Great work.