I think you missed the part where Simon tries to blame everything on Robyn. It was the scene just after she uncovered the PI files, and just before Simon went to administer the beatdown on Gordo.
If you look at the earlier conversations in the movie, they don't seem all that damning/bad at the time, but when you look back at them given the context that is revealed later on, you start to see exactly how controlling and manipulative Simon really is towards Robyn... he's just really good at it because he's had his entire life to perfect it and become really slick when delivering it all.
I do agree though... when you evaluate all of these things/conversations as one-off's it makes no sense for Robyn to leave. No one of sane mind would leave their spouse for doing any one of the individual things Simon did. Everyone has moments of weakness where they make bad judgment calls.
When you mesh it all together though, it makes some sense as to why Robyn would want nothing to do with Simon.
He's manipulative, he lies, he deflects, he is violent, he is ruthless for his own self interests, and while he's never physically beat up Robyn (that we know of)... he's shown that violence is always on the table as a solution to whatever temporary problem is in his way.
This isn't something that has manifested itself later on in life either... he's constantly been this way for decades. It just took the events that transpired for the revelation to occur within Robyn's head.
He also constantly tried to throw Robyn's own safety and well-being under the bus in order to avoid what might have led to very minor setbacks in his life/career. He put her and their child in significant danger by not being forthcoming about Gordo and the past incidences surrounding Gordo. Ditto with Danny.
The early parts of the film also lead into how manipulative Simon is (though subtly)... specifically the discussion about Robyn returning to work. Re-read it and you can see how self-centered Simon actually is. He gives her the illusion of his support, but then follows it up with the backhand of "I mean, if you want a family though... you probably shouldn't do that, but who am I to tell you anything?"
He's being very manipulative... even if it's in a very subtle/under the radar way.
Again... taken out of context and viewed as a one-off conversation, he's not doing anything terrible. Mesh in with everything else he's done/does, you can tell what a scumbag he is. It just took Robyn a really long time to put the pieces together.
http://www.springfieldspringfield.co.uk/movie_script.php?movie=the-gift
Robyn: Very nice. Isn't it?
Simon: Yeah. You should see upstairs. You should see Kevin's office. That's nice.
Robyn: Uh-huh.
Simon: But this is, it's pretty great. Yeah. Here they are.
Robyn: I cannot believe these guys are your bosses.
Simon: You are my boss, honey. Let's be clear. These guys just run the billion dollar company I work for. You know they've been multimillionaires since they were teenagers?
Robyn: Mmm-hmm. Crazy.
Simon: Yeah, once upon a time, the crusty old men ran the companies and the teenagers were down in the mail room. And now it's the total opposite. But I'm going to make it upstairs before I'm too old, as long as Kevin sticks to his plan of moving on at the end of the year. Then I get a little bit of consulting expertise from you, I'll be all set.
Robyn: Keep growing the beard. Start wearing sneakers to work.
Simon: Maybe get a tattoo.
Robyn: Yeah.
Simon: All good ideas. I'd look good in those glasses, I think.
Robyn: Hey, do you really not want me to go back to work? Are you still worried?
Simon: That's not what I said.
Robyn: No?
Simon: No.
Robyn: You know, we moved to the suburbs and... Yeah. For a fresh start.
Simon: Honey, I want you to do whatever you want to do. As long as you stay healthy, you can open an office in every major city in the world. I want you to start rebuilding the business. You know, what do I care? I just don't want you to be stressed, honey, because that's when those other things can happen. Yeah? Especially if you really want to start a family.
Robyn: Okay.
Simon: Did it sound that bad?
Robyn: No. No, I'm just being silly. Let's get back to the party.
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