IMO, you need to quit worrying about everything being "fair." You're now a partnership, not two individuals. Sometimes you will work harder; sometimes he will. Sometimes you'll spend more; sometimes he will. The important thing is that together you define your common goals and both work toward them.
As an example only, what my DH and I do is to automatically transfer a certain amount each month to separate accounts for our blow money. This money is for us to spend or save as we like. It typically goes for hobbies, individual entertainment expenses, weekday lunches, things like that. A couple of years ago, DH was getting more blow money than I because he was working a job that involved a lot of driving, and it was more difficult for him to pack a lunch. Now he's working at a single job site, so we've gone back to making it equal. To us, that is "fair."
Again, IMO, you are treating him like a child. Yes, he has made some foolish money decisions, but it sounds like he agrees that they are foolish and is committing to being more responsible now. The whole "you need to save more because you're behind me" and "I won't consider a house until *you* have enough savings" stuff just sounds petty to me. Set a goal for how much to save as a couple, and work toward that goal from your income as a couple.
I hope this doesn't sound too harsh. It's great that you are teaching him how to manage money better. It sounds like he needs some of that, not having gotten it from his own parents. I just think there needs to be more accepting where he is now from your side, just like he is committing to do better going forward on his.