Who the hell thinks Ash is a strong woman?
She's an emotionally crippled kid who never learned how to interact normally with people. Which isn't really surprising given her family and the fact that most men she associated with were middle aged perverts who were willing to sleep with an underage prostitute. She is shown to regret her actions and would like to fix things with her sister, but isn't strong enough to come out and say it. Her bitchiness is obviously just a defense mechanism.
As for her being independent, she just spent the last couple of years in juvenile detention under strict supervision. Now she lives in a halfway house under guidance and curfew. The first job that she was given (she didn't get it herself), she wasn't able to hold down and the one Sam got her now, she can only keep because the owner is even crazier than her. But even there she isn't actually allowed to work with customers yet.
There is absolutely NOTHING strong and independent about her.
As for the MC, why would anyone expect him to be super confident or good with women? He spent his entire adolescence locked up with zero contact with them. He has some boyish charm, a good physique and a big D, but he has zero idea what he's doing. He's just winging it and getting lucky.
Personally, I like him. He is inexperienced, but not an idiot. And (depending on the player's choices) his heart seems to be in the right place. Him not being overly cocky and pathetically "alpha" like some guys around here is actually a big plus in my eyes.
Dev did good in my book.