"Never hurts to try!" And it didn't. Because it was Elena and so of course she would try. And given her whole wanting to try and have a normal life, that fit right into that mold.
"People who are desperate, or who don't think he'd actually do it? People who think they can outsmart him?" People could do a lot of crazy things when they wanted a deal. Elena had been prepared to die when she renegotiated her deal with Elijah. She knew that he wouldn't let her die, and she knew her being a vampire would ruin it. She knew that she would do anything for Jeremy if he showed up. But usually it was the people who were underestimated who could get away with things like that.
"Seconding the things work differently depending on the world. Especially since there's no proof you'll even remember this place if or when you get sent back." There was no real need to go into what Elena did. She tried to live a normal life. She wasn't in Mystic Falls, she wasn't always waiting for the next attack for her blood. Crazy things happened here, but she still had more of a shot at a normal life than she'd had ever since her parents died.