Ahh, the mommy wars. Gotta love them, eh? I think the choice is an extremely personal one, no matter what the decision is, and I don't think there's any right or wrong answer. In the end, the most important part is that our kids are happy and are being raised to be "good" kids.
If Emily has a means, regardless of where it comes from, of staying home and not working and that's what she wants to do, then good for her. Where her money comes from has nothing to do with me and doesn't impact me in any way. In fact, I could care less! She gets to stay home and drive her daughter to practices and bake cookies for the team and that brings her happiness. Good for her.
As far as who she's dated - when you're part of a certain social circle, you tend to date people of that same social standing. It just is what it is and is mainly due to who you're exposed to. If I wasn't married and my friends tried to fix me up, I know they wouldn't be setting me up with a trash recycler or something like that. And if I met someone at the grocery store, they'd probably also be around the same social status b/c of where we live. Again, that's just the way things are. So I think it makes sense that Emily has dated who she has in the past.
I like Emily. I liked her during Brad's season also. And I'm cheering her on as she searches for someone to fill a void she's had in her life these last 7 years.
Sidenote - re: the cookies and orange slices. I'm sure the orange slices were for halftime and the cookies and juice boxes were for the end of the game. For soccer, the kids get things to eat/drink at both times, esp. when it's so darn hot down here.