"Damn women...always go for the Wookiee..."
Do you ever feel like everything that's anything that could happen to Han and Leia has already been written and written well? It's almost like when they remake a movie that was perfectly awesome to begin with (like Arthur - IMO), it almost seems doomed to failure from the start - always to be compared to the original or to someone who had done it better.
This is definitely how I feel about trip to Bespin stories. I have read so many spectacular stories for that trip that I feel: 1) that I could never do any better and 2) that there isn't anything new to add to it. But then I read someone else who has braved that time period and they add something new to it that I had never seen or thought of before and I think, hmmm - it is possible (just maybe not for me!)
And then that is what I think is so great about writing. How we all bring our own unique perspective, personality and voice to our stories and that is why I always encourage anyone who even has an inkling to write something down, to just do it. I know it's difficult to look at a string of words that you have laced together and not find fault in them, or think that they aren't worth another person's time to read. But, believe me, in the majority of the cases that just isn't true. If you have something to say, chances are there are people who will enjoy listening to you.
I guess my favorite time period for Han and Leia is the time between ANH and ESB. It's a good chunk of about three years where their relationship blossomed from strangers to two people who obviously have strong feelings for each other that are fighting in the middle of a busy corridor. I guess the possibilities of what could've happened between them during those three years are just about endless.
After then, of course, you have post-ROTJ where the world really just opens up for you because you are not restrained by the confines of the movies any longer - at least not like you are when writing during or in between the movies and trying to keep your story 'canon'. But just that open-ended possibility can be intimidating/daunting as well. I mean, they could live anywhere, do anything, and meet/mingle with anybody. Which brings us to the the EU story line. This might curtail your freedoms, but it also gives you some characters and story lines to work with that can make it a little easier.
I sometimes wonder how other writers decide what they are going to work on. For me it is usually the story that comes to me first and I am not intentionally trying to write in a certain timeframe. Except, I guess, for my post-ROTJ storyline where I am diligently trying to come up with 'what happened next?'. How does it happen for you guys? Do you let the story guide you? Or do you start with the timeline and brainstorm ideas?