Well, if they're Jedi, they - or one of them - could be assigned to sort out some kind of trade dispute, or take down a crime lord in some system, and run into Karrde/Skywalker that way. That'd set up a nice conflict, too, if they're working against each other or maybe are forced to work together. You could even tie it in with canon if you have them take on Jabba, because Jabba is behind a major drug feud or something somewhere, and maybe Han is indebted to Jabba like in canon and has to fight him as well? I don't know if any of that works within your setup, it's just the first thing I thought of. Jedi tend to defend the law, and smugglers break it, so that'd be the obvious conflict/means of getting them together, I guess.