Hey I completely agree with everything you said and honestly because I had an experience with grooming in the past I always felt weird about Lester's feelings for her. Like even though this is a fictional story that doesn't negate the fact that grooming in general is such a thing that should be frowned upon.
Yes but it's not like he tried to do things to her or anything. He knows his feelings for her and he knows how to keep himself away. And it's not like he planned this to happen it's just happen. You can't help who fall for. And I'm sure that she was the one who suggested to become a man in order to sell her clothes. He didn't plan to fall for her or anything and it's it's not like he has bad intentions towards her. And since he knew that if she stayed a women she would most likely fail because she's a women so i wouldn't blame Lester if he thought that she wouldn't succeed as a women and not just a women but a commoner.
When he first saw her he didn't really judge her off her gender it was only until when he saw her talent that he understood that she was talented. And because there was scams like faking talent before he didn't know weather to believe her or not when she said she had something amazing to show him. But overall this is fiction.
Just saying if Lester wasn't conventionally attractive then y'all would hate his guts. What he did can be considered grooming considering he took Yuri in as a minor (mentally she wasn't but her body is and that's what counts no matter how "mature" a person is, a minor is still a minor and to everyone in that world she was a minor at the time we the readers are the only ones who know of her past life). Even if she is mentally an adult, she was still vulnerable as she said. Lester was a grown man with money in a position of power in a highly misogynistic society where women have very limited power and roles. She was a poor preteen girl who left her home on her own to pursue her passions. She was vulnerable. He took under his wing and transformed her appearance to better pass the stereotypical idea of what a man looks like in order to pursue her passions and she's stuck in that mold in order to keep doing what she wants to do in life due to the world setting being the way it is. Misogyny won't go away from one brilliant woman doing brilliant things. If that's the case then the real world would be a safe place for women and we'd be recognized truly as equals. But it isn't and even after thousands of years of badass and brilliant women we still gotta fight for body autonomy in the U.S. amongst many other things. It just doesn't work that way y'all. She wouldn't have been able to change the whole world or possibly even easily been able to do what she does as a woman. Her feelings and trauma surrounding her gender identity and her situation are valid and very realistic. I'm glad the manhwa addresses that. I have lots of mixed feelings for Lester tbh and I am incredibly glad he isn't the ML. Like idk I feel like everyone will say it's a stretch for me to say he is a bad guy but realistically, in the real world, he is. We see that shit happen all the time. So yeah. That's just my thoughts on Lester rn