I reckon Tybolt has blown his chances with Jill. By forcing her hand with the blackmail, he's only pushed her interest further away. She even laughs along with Josy at TYbolt prosthetic teeth being knock out!
Rusty, he definitely made a bad first impression, I mean he should have at least read Romeo and Juliet! And although we didn't see it, we got the second hand story from Jill that they did have a date and he blew that too.
But the new and improved Rusty definitely seems Jill's type, even more so that the mc. So I'm gonna say Rusty.
I do wonder if all the "shipping" motherfuckers will get their day. When DPC's magnum opus finally comes to an end, will we get an epilogue coving every single character, LIs and others. That'd be cool. Of course not every one of them should be paired off, just generally how did they fair at college and what direction did it point them onto in life.
Unlikeable visually, or through his actions?
Visually he's pretty much on par with all the other weird looking mc's out there, and his actions, depending on your style of play, I thought he was more or less an ok dude.
One thing that I find typical in most of these games, is the mc is usually just a shell. He doesn't usually have too much of a personality, that way you can imagine your own preference there. In the games where they make the mc more aggressive, he almost always comes across as an asshole, but if they make him too nice, he comes off as a pushover.
It's rare (as in I've never seen it) that the mc is given a strong, positive personality. Maybe a backstory event that provides a strong emotional link to the mc would be useful (and the mc's sob story to Bella didn't really cut it), but that'd need to come up early on in the game at the risk of losing an audience that are there primarily for the porn.
CoBD probably does it better, but then really the mc is such a cliche, typical film noir character (DA took that to the extreme).