I generally do AU with Madison involved, considering we never see her killed on screen. I have plot suggestions on my journal. I have a huge weakness for this pairing. The most common one I've done is post season-3 with Dean in hell, but I'm willing to work around it.
And when you say, sticking Dean with kids...what do you mean? My muse gets kinda nervous with that thought. I love Daddy!Dean or him being a father figure/big brother to some kid, but never actually rped that out.
Do you have AIM or some kind of IMing program to plot out on?