I wrote a reddit thread to try and find someone with similar experiences as me but the general consensus in the comments seems to point more towards a botched job, even though the artist is quite reputable and I've done decent research beforehand. This may be because of my skin, maybe not.
To clarify a little bit, I've had a minor form of Alopecia Areate which was treated a few years back with a corticosteroid cream and the hairs have pretty much all grown back afterwards. I do have a few scars on my head, one from birth, a few from slamming my head into things. I also do wear a headset a lot, both during my commutes, my desk job and my gaming sessions.
So far I've mostly used a clipper without guard to cut tmy hair, I'm gonig to purchase an Andis T-Outliner for a closer shave, maybe that will create a better result. I'm trying to stay away from head shavers and razors as I don't want to upset my ,seemingly already fairly sensitive, scalp any more.
Edit: I'm also a little on the fence about the hairline itself, I think it's a little too far forward to my liking.
You can see more info here, both in the thread as in the comments. More pictures as well: