It all depends on how horrible you want to be to your character, and why. If you feel it's necessary to repeatedly ruin him over and over again, then go for it. Just bear in mind that if you do it too much, your readers will become desensitised to it and the final screwing won't have as much impact. A good screwing-over comes after a long period of peachiness. Then again, if you can manage to keep screwing him over and topping yourself each time, by all means go ahead.