Thus, there was always some ambiguity about just how much time passes between the movies of the original trilogy. It was generally accepted among my friends that 2 or 3 years passed between the first and second movie—and this was later backed up by the 'official' timeline. This passage of time seems most obvious when looking at Luke—who has gone from a 'raw recruit' in the first movie to the Commander of his own fighter squadron. Han's presence, however, throws a bit of a wrench into all of this—because if several years HAVE passed, you'd think he would have at least tried to settle his debt with Jabba. But maybe that can be explained away, too—maybe he tried to pay the debt but Jabba raised the 'interest' on it...or...whatever. In any case, most folks seemed cool with the idea that 'a couple years had passed' and so was I.
Where things got a bit confusing was the timeline between (and indeed DURING) the second and third movies. In Empire Strikes back, we see two main storylines progressing—Luke training on Dagobah and Han and Leia on the run from Darth Vader. On he one hand, Luke's training seems to be taking weeks—if not months (at least that was my impression) while on the other Han and Leia seem to be traveling just a few days to Bespin—where they spend only a day or so before being captured. And yet, in the midst of his training, Luke senses their plight and flies off to help them. Does this mean that Luke only had a couple days training before leaving Yoda? If so...wow. Fast learner. The explanation I came up with was that...they just didn't show the trip and how long it took for Han and Leia to get to Bespin.
A really geeky (no, make that nerdy) site that I visit occasionally—Star Wars Technical Commentaries—had an alternate explanation for this supposed time difference between the two stories. One that is very interesting. What they propose is that since the Falcon's hyperdrive was out, they had to use sublight engines to make the journey—thus bringing relativistic physics into the picture. Simply put, to the folks on the Falcon, only a couple days passed while their ship was traveling close to the speed of light. Meanwhile, time for Luke was passing as normal and several weeks/months passed (I'd say at least two months). I usually don't like the more 'scientific' explanations for things. But in this case, it seems to mesh well with what we see in the movie. So why not?
And then finally, we come to the ambiguous time between Episodes V and VI. There are all kinds of stories (Shadows of the Empire being one such) that detail things that happened between the movies. And yet to me it always seemed strange that a period of weeks (if not months) had again passed. I mean, it wasn't as though Luke and Leia didn't know where they were taking Han. And yet we have this supposedly drawn out chase with Boba Fett trying to get to Tatooine and rival hunters and friends of Han trying to stop him. As little time as hyperspace travel seems to take in the movies, I'm surprised Fett didn't arrive at Tatooine on the same day he left Bespin.
In any case, even if Luke and the others did know where Han was, I can still see them taking some time to plan and prepare. Afterall, Luke and Leia were both commanders in the Alliance. They no doubt had SOME other duties to fulfill before running off on what was essentially a personal matter. I also always kind of thought that Luke at least went back to talk to Yoda, if not complete a bit more training. Meanwhile, Lando and Chewie could have been doing recon stuff, planning how to get Han out. It may have taken some time for Lando to get into the Palace and funnel information back out to his compatriots. So... okay, maybe now I can start to believe that a month or even two pass.
Of course, these questions of timing only came up MUCH later in my Star Wars fanhood. The movies are so great that it never really mattered WHILE I was watching them. Indeed, it wasn't until I started up my Star Wars gaming campaign that I decided to try and 'lock down' some dates to work with—as it was always my intention to run a group through the times of all three movies.
What's the point of this post? Well, just me rambling, I guess. And if you've gotten this far- HAH! Gotcha.