Why it Will Never Work:
Han's Looming Unemployment and Deteriorating Self Worth.
Han and Leia overcome checkered pasts, experimentation with incest and a general distaste for one another to form a love so powerful it couldn't all be included in the final cut of The Return of the Jedi. Also on the cutting room floor: the 4am fights, alcoholism and murder suicide that inevitably follow.
We totally understand that the "Princess and the Bad Boy" element is what was supposed to make us swoon--half of Hollywood romances are based on that. So let's say that they can overcome the distance caused by differences in socioeconomic status ( which psychologists tell us is no small barrier). But that can't bring Han and Leia down, they were united by the cause of the galactic rebellion! She respects him as a brave and passionate fighter for all that she believes in, and is entitled to!
Ah, about that. See, the war kind of ends when the second Death Star blew up. These two had never met before the war--literally every single activity and conversation they've shared has revolved around it. They don't know each other in any other context (this sort of thing is one reason why marriages hurriedly rushed into during wartime don't last as evidenced by divorce rates going up after ever major war since divorce was invented). Soldiers don't always adjust well to not being soldiers.
But that actually leads to another problem. What is Han's job when there isn't a war on? He's a smuggler, a guy with a shitty car who owes money on every planet and always shoots first in a fight.
And according to this picture, with his dick.