So yeah, I'd say that the myEdwin is a far cry above Ian thus far, he's always tried to make the best of whatever shitty hand he's been dealt, not taken advantage of others (some of it is definitely mutal taking advantage of each other due to the poor circumstances some of the women are in, we all know the deal) and kept his word when given. Now that doesn't mean he's a white knight by any means, but he doesn't play people false, or lie (just may not tell them everything going on)
I like your playstyle and believe it's relatively close to mine, except the lying part (i believe it's necessary in my run), which i'd like to call 'Tainted White Knight'.
MyEdwin really tries to help those girls which he has in his care, but he also has to face the reality that he has to handle them for the exhibition. MyEdwin realizes his influence and power is at the moment very limited, so same as yourEdwin he needs to make the best out of the hand he has been given.
There is a relatively old post i'd like to share in which i explain my approach with Rosie and Feli for instance (slightly edited):
"Back in my youthful days i was a member of a club, which central purpose is to provide help to drowning people as a first responder and to assist professional rescue services on water based accidents (at the Sea, at Lakes and Public Pools).
So the thing is, drowning people often are understandably panicking, thus endangering and hampering the rescue process, and in worst case this can lead to the death of both the accident victim and the helper.
So the rescuer is allowed to make them...
comply, including stuff like dislocating joints, breaking an arm or choking them to unconsciousness. Literally 'the ends justifies the means'.
I took a similar approach with Rosie, making her docile and following my lead, she doesnt need to
like Edwin to profit from his help. It doesnt look like it, but i am indeed fond of her, and i plan to crawl back out of the cellar relationship wise. I do also believe, that this harsh approach hardens her resilience against the trials she has to face, and making a deal elevates her out of a dependent and receiving role, because she gets something for giving something. MyEdwins help is not charity, it's a commodity she earned.
The same stands true with Felicias Sugar-Mama Date: i was tempted to do it for free, because it is obviously nicer and helps her with her confidence, and i really like her as a person, but opted against it. Experiencing the power she can wield with her money, being able to reverse the role she was used to her whole life, may also gain her some confidence.
Not to forget, with his own funds at his disposal, without having to ask someone for it, MyEdwin can act faster and more freely if the necessity arises."
As you can see myEdwin doesn't try to be an asshole, but sometimes he believes he has to be an asshole to be in better position to achieve his goals, which are - since the last update - to bring down Kathleen and Chuck (formerly only Kathleen). And since he has chosen the probably most dangerous and resourcefull owners as opponents he has to be extra careful.