I too struggle with the "diet-is-supposed-to-be-painful" syndrome, but I've been trying to convince myself that I'm not dieting, instead I'm adopting "healthy habits", which has helped with my overall attitude. I don't know that what you're suggesting is unhealthy, but it could end up being too much of a pain in the butt to work well for the long haul. Do you have to exercise before you eat anything? And what happens if you don't get to the gym because you have something else going on (wedding, vacation, funeral, etc etc), do you only get 1,000 calories? What if you tear a muscle and are out of the gym for a month? For me your plan would be prone to failure just because I wouldn't get to eat dinner if I didn't get to the gym on a given day, which sooner or later would mean a swan dive off the diet wagon. But you might have a lot more willpower and self control than I do.
I base my caloric intake on what the fitday weight goal tab suggested (well sort of anyway). I shoot for a calorie intake of 1,350-1,600/day and a calorie deficit of 500-1,500. It varies everyday, but my strategy needs to be flexible in order to work for the long haul.
Starting weight: 244.6 lbs. 10/01/09
Pounds lost: 80.6 lbs
Current weight: 164 lbs
Goal weight: 120 lbs
Weight to go: 44 lbs
Goal Date: 1/1/13