At first, I was doubtful about the 2nd story's dark haired careless freeloader. He's useless, he's lazy, and he just decided that out of instinct, he'd like to sleep with the bar owner, his reason being that anyone would do at that point. He just sounded so trashy and frivolous, not the type you'd depend on anything.
However, after seeing the next chapter, he had begun to redeem himself, in a way. Well, it's thanks to the bar owner, but now he's making a change. He's finally working and is actually good at bringing in customers. Not only does that raise his value in himself, but it decreases the trouble he brings about by just not taking care of himself or doing things right. Finally, he's doing something in exchange for the priviledges he's given, instead of taking it for granted, even as he lives in someone else's home.
Not only is he starting to work, he started being more serious, too. Instead of just "you'll do" it's become more like, "I want it to be you". He's trying to improve himself, and he's become genuinely interested in the bar owner.
I appreciate his resolve. He's not the most awesome person, but I've seen some characters in stories who are like him and don't bother changing themselves. Even worse if they're dense.
His core personality of being carefree and lazy hasn't really changed, but the fact that he's decided to work harder and have come to seriously like someone means he's changed considerably, from thinking it's a pain to work(when in the first place he was relying on someone to give him food and shelter for nothing) to thinking he'd like to work harder if it means making the bar owner happy.
An example of a guy I can't help but think about in here is Rock, of Harvest Moon DS (and DS cute (for girls)). He's the village's local playboy, and is so full of himself. He lives in an inn with his mom, and doesn't do anything to help out. No, seriously, he spends him time wondering, daydreaming, and admiring himself. when he marries the girl who likes him (Lumina, the rich girl who lives in a golden mansion and is teased by him) He doesn't do anything -his lifestyle doesn't change, he just got richer.
Otameshi Delivery Lover