Well, how devoted a "family man" can you be if you start in jail?
Right. It is perfectly possible to commit a crime in order to defend or support your family. And depending on the culture of the times and the class of the person committing the crime, such a crime may be dealt with leniently or extremely harshly. Are we supposing that Skyrim has Sapient Rights legislation to ensure fair trial and proportionate punishment?
Again, as it has been stated a million times, role playing doesn't mean you "live life in a game" as you want it, it simply means the character you control plays a role within the confines of the story and the setting, and there is no main character "family man" within the confines of Skyrim's story and setting.
I disagree. To my mind, a roleplay game may provide you with a character (eg. Geralt of Rivea) or it may allow you to define your own character within the gameworld. The Elder Scrolls games make a big deal of not limiting you to a specific character class or type, and don't force a backstory on you (leaving you free, in theory, to make up your own). The series makes a point of letting you go where you want and (as far as a quest system allows) do what you want.
It seems entirely in keeping with the spirit of the series that it should allow you to provide whatever backstory you want, or at least to build whatever character you want. I've always thought that it is a failing of the Elder Scrolls (by which I mean, a failing to live up to its own ideals) that from Morrowind on the only personality you can actually give your character is that of a socially isolated, emotionally dead mercenary. The only motive you can have for taking on quests is either money or survival.
I don't expect this to change in Skyrim, but it would be nice if it did. Obviously, being about player choice would mean not forcing anything on players, but having the option available.