I think he would've been proud. A normal life is something Dean never had, so it would've been nice for John to see that.

I think he would be happy, but realistically you have to expect him to be at least a little upset by it. John would have thought that Dean was being reckless and putting these people he loved in danger. He would have seen parallels between his life with Mary and Dean's with Lisa inevitably and he would have feared for everyone involved. He would have known that it couldn't last and also be sad that his son was going to make an attachment to people he would one day have to leave. So while I think he would want Dean to be happy, I think he would want Dean to be realistic in that goal as well. I can see John being a Dean/Jo shipper because he would want someone that could make his son happy, but who could also understand his job and protect herself without being a liability to have around. Or that's how I imagine John would see things.

He was mad at Sam to opt out so if Dean did something like that with his brother in the pit i guess John would be a little angry.

Neither, I honestly don't think he would have gone back to them if John were alive he would have still been in the "family business" kill evil along side his dad & Dean would have been happy about it.