When I said "take a chance", I was referring to not putting the family in any position where they wouldn't make bank in his absence. He didn't want his family to have to give up their home or a car. He wanted them to have extra. To not struggle. To be set for life. That's what all fathers/husbands want. To feel as though they are providing. To know their family never has to pinch pennies. Obviously there's a risk. At first, the inherent risk to himself seemed meaningless as he had a death sentence anyway. I don't think anyone was an honest threat to the family until the cartel became involved. By that point, he was too far in to back out.
Gilligan said most recently that his goal was to show how Mr. Chips could gradually turn into Scarface. That's exactly what we've gotten. I'd hardly say Walter had reached that point in the first season.
To clarify, I'm not picking your statements apart, as I know that's not likely your goal either. It's fun to go back and forth and theorize, like with any popular serialized show. I just personally empathize with Walt more than Skylar. But the heart of the show is Jesse. I'm surprised how attached I've gotten to him. That's how I see the current triangle: Walt is the brains, Mike is the balls, Jesse is the heart. While I have sympathized with Skylar at times, she's made too many irritating mistakes for me to not want to punch her in the head. At least Walt's goals end with money in the pocket (to note, it's obvious he's drunk off the power he has now more than anything, but as we've seen, the money does matter him, even if it is only a tool for, again, more power). Everything she does seems to be strictly destructive. I understand that that is how the character is being written. Emotionally, that's how I'm taking her: an annoyance. I know she's suffering from shock and perhaps even some mental illness or belated postpartum issues, but her actions just wreak of uselessness. Another obstacle to overcome. I'm not saying she deserved to be thrown into this situation, only stating that the way she is dealing with it is unacceptable. Sure, who knows what I'd do in the situation, but this is television. I'm not so much concerned with that. We need characters to identify with and be opposed to, and there's not really any villain right now. Skylar is essentially the current antagonist. I wouldn't be surprised if that's how the show shapes up.