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It sounds like fun. The elephant of the room of course is: what if events in the flashback don't go "as planned"? For example, if someone is supposed to have run away during the flashback but gets tripped and beaten unconscious. That sort of thing can happen if you actually play it out.
That's not a disaster, as long as you and your players are okay with it. Just say that what was previously "known" may be the version the PC likes the remember, while what exactly happened wasn't quite the same. Maybe the PC is ashamed to tell that after being captured he was interrogated and betrayed some secrets, but later managed to escape.
The trick then is to keep your flashbacks short enough, and have some offscreen time between the flashback and current history, so that there's time in which all that can have been fixed.
How about bloodrager for the druid's sister?
Does anyone have experience with Flashback sessions? Can you keep it interesting when, it being a flashback, the outcome is already known?
Why do you intend for your flashback scenes to be one-on-one? When I've run flashbacks, I've done it with the whole party present. Obviously, that puts some restrains on the scene - it can't be very long since that would be boring for the other players. But the benefits outweigh the drawbacks.
Rigid, rules-heavy games such as Pathfinder don't lend them self easily to narrative tricks like flash-backs, as you've discovered. They are, however, possible to play out.
The outcome being known doesn’t need to be a problem. Look at Montsegur 1244. The whole game takes place during the siege of Montsegur, inevitably ending with everyone inside - including the PCs - having to choose to convert or die for their heretical religion. The outcome is set from the beginning, and yet they managed to write a whole game about that. There's plenty of other examples, within our hobby and outside of it (how many times where you surprised when James Bond managed to survive and beat the bad guy? Yet that don't seem to spoil the films for the audience).
Sometimes the journey is more important than the outcome. Flashback scenes can be an opportunity to establish a character, develop her personality, motives and quirks. It's paramount to run such a scene with everyone present. Sure, the player can need a chance to flesh out her own image of the character, but those who really stands to benefit in their understanding of a fellow PC are the other players. Sure, you can tell everyone that you're looking for revenge for the murder of your brother. But show is better than tell.
A flashback scene can be very short. They need not contain much action. They can be a single conversion, where an NPC, played by the GM or another player, makes inquiries about something that has happened - or is planned to take place - for the PC. The player gets a natural way to explain her PC with her in-character-voice.
Getting clues and contacts are not out of the question, though. Let's tale your first idea.
My plan was to play the original theft of the scroll, giving her some info on the man and how she would be able to find him in the future
If I where to GM this, I'd do it right at the start of a normal session or in a break in the action in the middle. I'd tell the player: »you where challenged to steal a scroll, describe where that took place.« I might run that scene through, playing the man issuing the challenge. The theft is rather uninteresting, it has taken place. The player could describe how that went.
But the important part is the PC being an outcast and her quest for the man. So I'd tell the player »You once came across an old sage who you thought had information about the man who tricked you« and I'd play out the conversation between the PC and the sage. Thus, I can both give clues about the man and get the PC to show her colours - the sage can ask questions about why this scroll-business is so important, the sage can withhold information - pushing the player to show how the PC solves problems etc.
Any idea on how to give awards for such a session? XP and cool gear would then have to materialize in the 'present' day to be much of a reward, so what else could be rewards?
XP don't really materialize in the present day, do they? At least, they don't need to be thought to do. Unless the character gains a level directly after, the XP can easily be seen as having existed all along. I would nonetheless not give out XP for a flashback scene with a single participating PC, since I like the party to be on equal level.
Actually, I wouldn't give out any reward for a flashback scene at all. The scene should be a reward in it self. Although, contacts and clues established during a flashback can be seen as rewards, and I'm all for that.
Bonus traits might also be a good reward for a flashback, or story feats.
I second the Character Traits option, though some of them may be difficult to implement with their current flavor; still, it shouldn't be too difficult to alter what that flavor actually is to suit the needs of your campaign.
For example, a lot of people joke that the Reactionary character trait, which most everyone takes, makes everyone a child who was bullied when they were younger, and just ran, based on the flavor text "You were bullied often as a child, but never quite developed an offensive response. Instead, you became adept at anticipating sudden attacks and reacting to danger quickly."
I'd prefer to think of that as an anecdotal example of why you developed such quick combat intuition, not something that should've actually happened. Though this is one of the easier ones to reflavor; others require more planning and consideration.
I'd also consider the Story Feats, especially in relation to current events that may involve the character's background (i.e. they caught up to the jerk who stole the Elder Scroll), here. A lot of them are usually in relation to a character's background, so when they complete their respective background sessions, I'd consider tossing them a story feat, and if they end up resolving whatever issues that cropped up from their background, give them the completed effect of their chosen Story Feat.
The only possible reward you have to offer is information. Let them find something out, and frame it as someone telling them what happened. That also allows you to use the El Shaddai and Dragon Age II solution to things going wrong: The one telling the story says "No, that was not what happened." Note that you really are not in a hurry to do this. Let the PCs explore something of what would have happened first. Done right, you can give them something they had no idea about, that makes the scene more complex.
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If only a few of your players are there, you can also give the other players NPC roles to play. Having a few people subbing in as NPCs allows you to portray conversations between multiple NPCs and the PC with much less schizophrenia. Plus, some players really get into it.
This works better for RP-heavy stuff of course, because you can just tell them "you're so and so, known for [something], and you want the following in this scene" and let it roll.
