Thoughts on Alternate Realities, Self-Publishing, and Pottermore

I've always wondered... what would life be like if certain things didn't happen? I know I've talked about this before, but I recently started mulling over the idea further.

A friend and I had been trying to decide what to roleplay over instant messenger. For several years we've been using the same family/universe of characters, and slowly expanding on them. We have three generations of this family, and were running out of possible plot ideas. A thought had struck me the other day, about what would have happened to our characters had we not chosen the storylines we did.

For example, my character Casey almost loses his wife when she's giving birth. We originally planned it that his wife would survive. But thinking back, I wonder where he and his daughter would be if his wife didn't survive. Sure, he's my character, and I can write him a happy ending if I want; but that doesn't provide any amount of growth or depth. It just ties up loose ends. I'd rather like to see the struggles he goes through as a widowed father; how he copes with this sudden loss and sole responsibility; what he does when his daughter starts inquiring about her deceased mother. And what he does when he starts wading into the mess of dating when having a child.

There were other alternate universe/plot turns we came up with that gave us very interesting roads to eventually travel down. So, we've decided to go back and play these out, just to see where we would take them.