I disagree. He comes from money. He sees it as a way of power. He gives Rory a house to live in and then expects her to be at his beck and call. BECAUSE SHE IS.
He is (or already has) becoming his father.

I thought he'd be married already. He didn't do monogamous relationships in the original series, until Rory. It wasn't surprising to find out that he's a cheater.
He obviously still has feelings for Rory, and I guess that's why they're still sleeping together? They can't get enough of each other, but I guess there's too much history there for him to try and make a legitimate go of it with her (though I'm not sure, I don't care about either character enough to look too deeply into it). I think it was up to Rory to outright ask for something more. He was the one who proposed to her in season 7 and she turned it down, and he probably can't put himself in that position, to be rejected by her again.

Except that he isn't. ASP ignored the entire season 7 and all his growth and him standing up to his father and cutting those ties. I am sorry but season 7 DID happen and Logan wouldn't be following his father's footsteps. Heck he wouldn't be following those based on the late season 6 that Amy herself wrote. The whole thing was uncharacteristic for Logan - especially considering he was in love with Rory and he would have married her if she hadn't said no. So given they fell back into a relationship there is no logic in him choosing an arranged marriage over the love of his life. The only explanation is ASP childishly decided to pretend a whole season didn't happen.

I don't think they did. He was still pretty much the same guy, except that he was sort of following in his father's footsteps which always seemed to be something he was against. I'm surprised he wasn't already married.
And she acted like I was teaching her about everything.

I would have been far more into it if neither of them were in a serious relationship. Like she said, what happens in Vegas stays in in Vegas, but I was picturing it more like 2 single people happen to hook up when they are in the same place. Old loves, still friends having some fun. But then they go back to regular life afterwards with no strings attached. Definitely through me off when they were both dating other people.

Ah thank you - I am not crazy!

But they kept mentioning her as a point. Logan was clearly still in love with her but he, like Christopher, had a path he was on that he was unlikely to get off and Rory, like her mother, wasn't ready to be tied down yet.
I find it uncharacteristic for Logan (I know, he used to be a womaniser but honestly he's the one more committed to this particular relationship as it's changed him) but not Rory. I think people give her more credit than she's worth and that Logan was just being portrayed as a victim of his circumstances marrying an heiress because it's supposed to be his path. (He says as much in the ladb hotel scene) but at the end of the day she likes her relationships etc to be Rory centric. Like Luke to Lorelai, Logan is gonna be there for Rory no matter what and she knows that safety blanket is there. That's why she keeps accidentally / subconsciously calling him. He's the guy she can say anything to and not be judged or downgraded in his esteem. He'll do her the favours and make the gestures and so long as she doesn't actually marry him she can pretend she's not a product of the same privileges he is.

It was even more messed up that Rory was on board with all that. So weird how the two of them were planning their hookups around Logan's fianc and how Rory kept mentioning her

Agree completely! Hated that storyline.