I'll talk about which three characters deserve a solo outing more than any other and perhaps try to match actors, directors and possible talent to make these outings something special.
3 - Bail Organa
Yeah. Bet you didn't see that coming did you? Bail Organa, played by Jimmy Smits, is pretty much the definition of 'background' character. He has about ten lines in the entire prequel trilogy, disappears and then is seemingly exploded when Alderaan bites the Death Star's bullet... made of lasers... and death. Why Bail then? Why not Moff Tarkin or the obscure bounty hunters or any number of background figures? Why does Bail deserve a film more than any other 'background figure', including all those terribly designed CGI tentacle-not-hentai-faced Jedi? Is he even worthy of having four rhetorical questions in a row? Bail has, in my opinion, one of the most important roles in the entire saga. He practically adopts Princess Leia, taking her away from Luke, and thus sets in motion perhaps the entire original trilogy's struggle of Rebellion versus Empire. Leia grows and lives on Alderaan with Bail to learn about the greater world before the Empire and slowly grows into the rebellion that Bail is involved in. Bail teaches Leia everything about the Empire and is then blown in to smithereens too, making it a not so happy ending.
How on Earth would this even be done, you ask. How could this even be entertaining? If we see Bail as one of the 'figures of glue' (the other being Obi-Wan) who take on new roles to facilitate the rebellion then we see them as forefathers to all of the action in the original trilogy. Bail's story could easily become one of trying to begin the Rebel Alliance while protecting the last grains of the 'new hope', building up the Rebel forces while raising Leia. Bail is arguably the true father of the rebellion and the film can see him perhaps having to pull a Walter White and shoot people in the face in breaking away from his stuffy political background into Rebellion mastermind. There's thousands of 'extended universe' material with this guy, including his manipulation of massacres and attempts to undermine the Empire, and seeing Bail build up the rebel forces would make for the perfect film to fill in the gaps. It could even end with him all aged on Alderaan saying goodbye to his adopted daughter and watching the Tantive IV (the ship at the beginning of A New Hope) fly off into the unknown with all of his new life's work and thousands of rebels disappearing off to go and claim back the Republic.
Talent: Jimmy Smits might not be up for this endeavor given he's ageing on a bit now. I would have Leia played by Chloe Mortez and Bail played by Steven Michael or maybe Sacha Baron Cohen, who is well capable of delivering drama. For who to direct it, I'm not quite sure. The film is about Bail descending into this mad, mad world of a rebellion and building up a resistance to the empire; it's about a journey from being weakness to hopelessness to hope. I can see Rian Johnson, of Looper fame, having a swing at this.
2 - Chewbacca
Chewbacca appearing in Episode III was... okay. It was a little bit weird to realize that both Luke Skywalker and Chewbacca have come into contact with Yoda and somehow Chewie doesn't seem to pass this information on to Luke. Not even saying "Hey. I met a lightsaber person once. He was pretty slick." We don't even have any indication through Han that Chewie knew Jedis and did the pew pew Clone Wars-ing. I could honestly see a film about Chewbacca becoming something of an Argo in which Kashyyyk (the Wookie homeplanet) is help captive by the Empire and the Wookies are forced in to slave labor. The entire film could be a prison breakout as Chewbacca attempts to unite the Wookies against the tyranny of the Empire's stranglehold. It'd be interesting to see Chewbacca begin as a rebel and perhaps he'd cross paths with Bail or a young Han Solo by the end, beginning their fruitful friendship.
The film would likely mirror the exact same structure of The Great Escape in Chewbacca and friends trying to escape from, essentially, a Prison Planet. It would be incredibly interesting, in my opinion, to do a film like this without sub-titles. I honestly believe that obscuring the Wookie language keeps the comedic elements and preserves the Wookies as utterly unique. When Han talks about what Chewie is saying then we have to somehow think that if Han understands the Wookie language then he must've been around them for a long time. Han was a smuggler and perhaps there's some cargo around Kashyyyk that he is in need of. The entire film could end with Chewie banding up with him to break through the Empire's blockade aboard the Millennium Falcon, just like the finale to Argo with 20% less Iranians.
Talent: Peter Mahyew is an absolute necessity. Getting Ben Burtt to do the sound design would be utterly essential as well. Whomever Disney picks for a young Han Solo would be nice for this piece too. I'm honest in saying I think Bradley Cooper or, don't slaughter me, Shia Lebouf could handle it. As for direction, I don't know if Ben Affleck would be up for something so 'out there'. I can see someone more affiliated with 'prison break' type stuff would be much more naturally suited; particularly Frank Darabont (who's worked on a few science-fiction projects himself).
1 - Qui-Gon Jinn
One of the many things I shan't ever forgive Lucas for, with the prequel trilogy, is the absolute misuse of Liam Neeson. Neeson is an incredible talent and one who can command a presence so indistinguishable from any other actor. To use him in a film which doesn't even have a protagonist is shameful, to then give Neeson a soul-crushingly empty character is double-shameful. I argue that the entire prequel saga feels lost without Qui-Gon's character development given we don't understand his 'worth' to the Jedi world and particularly to Obi-Wan. We never see their relationship develop, it's just assumed that we care. Obi-Wan definitely changes across the series and Gon's death is instrumental to catalyzing this change, but the man behind Obi needs to be defined.
Gon's film could play out like Batman Begins or Spider-Man in showing his rise to power. Perhaps having him search out for the beginnings to the 'disturbance in the force' and showing Palpatine's rise in the background. Heck, even have Qui maybe even have a period of exile. The film could perhaps focus around a bounty hunter force that is slaying Jedis throughout the Republic and Qui-Gon has to figure out exactly who is picking off the first line of defenses, before culminating in a battle with a rogue Jedi or something? Anything could happen. Qui-Gon's story is one that needs to be told given it can not only build the character of Qui in time for Phantom but also put in place all of Obi-Wan's future lessons and indeed set the scene, in terms of the political situation, of the entire prequel trilogy. It all begins with Qui.
Talent: Duncan Jones (of Source Code fame) to direct. No question. The man nails characterization. Christian Bale could pull off a young Liam Neeson quite well, but Josh Pence actually portrayed a younger version of Ra's in The Dark Knight Rises so casting him would be perfect. I wouldn't have Obi-Wan appear as a child, because child actors are child actors, but perhaps have him pass on to Qui-Gon's care as a teenager. Logan Lerman might be a good choice for a tweenaged Obi-Wan then.
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