If we're talking crazy, then he needs to carry a burlap sack that has the head of a certain wookie friend in it. That he talks to. But I am serious: the more I think about it, I don't want Solo. And I love Han Solo. But...
He's got his own planet, Although it's kind of wild. Wookiees love him. Women love him. He's got a winning smile! Though he may seem cool and cocky, He's more sensitive than he seems, Chorus: Han Solo, What a man! Solo. He's every Princess's dream!
I think their relationship is doomed. He's the flyboy badboy of the youth she didn't have being raised for public service. He'll get bored with the duties and she'll get bored with the attitude.
I'm talking 10+ years later. And I didn't say he returns to smuggling, just that it's doomed, especially if there is an extended time of peace.
With the love of repeated dialogue and situations in the franchise you could almost imagine him being confronted by Luke's son. 'No. I am your father'
Do you have any actual indication that these iconic roles will be recast beyond some self delusion that it's all about "the demographics"?
No one seemed to mind that the OT had plenty of "old codger" Obi Wan. And no, Alec Guinness was not a hip name among teens of the time.
By the end of ROTJ, Han had become pretty domesticated. He could easily become similar to Lando in ESB while staying with Leia: responsible and diplomatic while using his charm to succeed in some larger role in the government.
And that's why I don't need to see him again. His story, his life of adventure, is over. Who would want to see a "successful" diplomat Han Solo? Sounds AWFUL. Lando, at least, had some shades of grey.
We saw him for 5 minutes at the end of a battle. Everything was still VERY exciting regardless of him being on the right side of the law. I would hardly call this domesticated. Let him be married and up to his neck in diplomacy for ten years and we'll see how happy he is with domestication. He's going to get bored and she's going to get irritated with his boredom.
All I ever read was the Thrawn trilogy but that was a long time ago and I can't remember a thing about it.
I would say the Thrawn trilogy were the only great Star Wars books. The author did a good job writing a believable Han and Leia married relationship too. Most of what happens later is pretty... well... stupid.