These are some things that I did in a roleplaying sense to do some more/change some quests.
I was thinking maybe for the Third Chapter of the story, when Ulfric captures the three thieves, and The Black Arrow is forced to join the Stormcloaks, he goes on the missions up to the Jagged Crown quest with the Stormcloaks. The Arrow is then informed that there was a raid in Windhelm by some of the guild members to rescue the three. When the Arrow finds out, he betrays the Stormcloaks and brings the Jagged Crown to the Empire and joins them to overthrow Ulfric for his underhaded tactics to get the Arrow to join the Stormcloaks. This idea also goes well with the connection to the Thieves Guild because it puts Maven Black-Briar in the Jarl's Throne.
Also, The Black Arrow can look into the rumors of the Dark Brotherhood during the Second Chapter. While doing a job in Windhelm, The Black Arrow hears rumors that Aventus Aretino performing the ritual to call the Dark Brotherhood. The Black Arrow listens to Aventus, and performs his task, leaving a single black arrow in Grelod the Kind, because he remembers what it's like to need help, and no one is there to help you. Then the courier comes, delivers the message and The Black Arrow meets Astrid, who has wanted to meet the Arrow after hearing about his raids and expertise as an archer. He weighs his options on whether or not to join the Brotherhood. In a way, he considers joining the Brotherhood because in a slight and twisted way, it's almost as though it's justice being brought to the people being wronged. During thw assassination of the Vampire woodcutter Hern. Upon the Vampire's death, he is then approached by the Dawnguard, who was investigating the possibility of Hern being a vampire. So the Dawnguard then extend an invitation to join the Dawnguard to fight the Vampires who are attacking civilians. He promises to join them, but at a later time. The Arrow continues to follow the orders of Astrid, who he begins to question her motives and allegience. When Cicero goes crazy, the Arrow let's Cicero walk away, because he questions Astrid's orders more and more. The Arrow then finishes the Dark Brotherhood questline.
With the Dawnguard questline, it is post College/Main Story Questline, and the Arrow is really feeling his old age. He however remembers his promise to join the Vampire Hunters, and so he goes to Fort Dawnguard to speak with Isran. Isran offers the Arrow a crossbow to help fight the vampires, however he declines the use of the crossbow, since he has difficultieshitting his targets and says that it doesn't feel the same as using a regular bow. The Arrow goes to Dimhollow Crypt and finds Serana locked away, and brings her home to Castle Volkihar. While there, Harkon offers the Arrow his power and the bonus of elongated life with the Vampiric powers. As Serana is standing there, worried about the Arrow's choice due to him seriously considering the possibility of a longer life, she starts to fear the Arrow joining the Vampires, as Serana begins to develop feelings for the Arrow during their trek to Castle Volkihar, was it because it was his blood that awoke her, or the fact that he didn't fear her, she didn't care. The Arrow however turns down Harkon and leaves/is banished frm Castle Volkihar. The Arrow returns to Isran with the news of the Vampires having the Elder Scroll and what went on in Dimhollow. The Arrow continues on the questline as is. During their adventures across Skyrim, the Arrow begins to develop his own feeling of attraction for Serana, and vows to protect her, as long as she stays with him. She incidentaly informs the Arrow that she made the same vow to herself. As they prepare to travel to the Soul Cairn, the Arrow finds out the painful way that he needs to be "dead" to enter the Cairn. Serana offers to turn the Arrow into a vampire, informing him that the act is "an intimate act", or putting half of his soul in a soul gem. Because of their feelings towards each other, they proceed with the vampire bite. While in the Cairn, they meet Valerica, she questions the Arrow's intentions. He claims that he will protect Serana, and she in turn defends him from her mother. They continue through the questline together, after the Arrow is forced to cure the vampirism by Isran, and attack Volkihar, kill Harkon, and rescue Valerica from the Cairn. The Arrow wears the Amulet of Mara, to show his affection for Serana, in hopes to marry her, she declines because of her fear of temples due to her past. They then stay together, even though she fears the temple, as though they were married, just without the ceremony. (I personally didn't cure Serana's vampirism, since her eyes look cool as a vampire, and really weird as a cured vampire.)
These are some things that I did in a roleplaying sense to do some more/change some quests.
I was thinking maybe for the Third Chapter of the story, when Ulfric captures the three thieves, and The Black Arrow is forced to join the Stormcloaks, he goes on the missions up to the Jagged Crown quest with the Stormcloaks. The Arrow is then informed that there was a raid in Windhelm by some of the guild members to rescue the three. When the Arrow finds out, he betrays the Stormcloaks and brings the Jagged Crown to the Empire and joins them to overthrow Ulfric for his underhaded tactics to get the Arrow to join the Stormcloaks. This idea also goes well with the connection to the Thieves Guild because it puts Maven Black-Briar in the Jarl's Throne.
Also, The Black Arrow can look into the rumors of the Dark Brotherhood during the Second Chapter. While doing a job in Windhelm, The Black Arrow hears rumors that Aventus Aretino performing the ritual to call the Dark Brotherhood. The Black Arrow listens to Aventus, and performs his task, leaving a single black arrow in Grelod the Kind, because he remembers what it's like to need help, and no one is there to help you. Then the courier comes, delivers the message and The Black Arrow meets Astrid, who has wanted to meet the Arrow after hearing about his raids and expertise as an archer. He weighs his options on whether or not to join the Brotherhood. In a way, he considers joining the Brotherhood because in a slight and twisted way, it's almost as though it's justice being brought to the people being wronged. During thw assassination of the Vampire woodcutter Hern. Upon the Vampire's death, he is then approached by the Dawnguard, who was investigating the possibility of Hern being a vampire. So the Dawnguard then extend an invitation to join the Dawnguard to fight the Vampires who are attacking civilians. He promises to join them, but at a later time. The Arrow continues to follow the orders of Astrid, who he begins to question her motives and allegience. When Cicero goes crazy, the Arrow let's Cicero walk away, because he questions Astrid's orders more and more. The Arrow then finishes the Dark Brotherhood questline.
With the Dawnguard questline, it is post College/Main Story Questline, and the Arrow is really feeling his old age. He however remembers his promise to join the Vampire Hunters, and so he goes to Fort Dawnguard to speak with Isran. Isran offers the Arrow a crossbow to help fight the vampires, however he declines the use of the crossbow, since he has difficultieshitting his targets and says that it doesn't feel the same as using a regular bow. The Arrow goes to Dimhollow Crypt and finds Serana locked away, and brings her home to Castle Volkihar. While there, Harkon offers the Arrow his power and the bonus of elongated life with the Vampiric powers. As Serana is standing there, worried about the Arrow's choice due to him seriously considering the possibility of a longer life, she starts to fear the Arrow joining the Vampires, as Serana begins to develop feelings for the Arrow during their trek to Castle Volkihar, was it because it was his blood that awoke her, or the fact that he didn't fear her, she didn't care. The Arrow however turns down Harkon and leaves/is banished frm Castle Volkihar. The Arrow returns to Isran with the news of the Vampires having the Elder Scroll and what went on in Dimhollow. The Arrow continues on the questline as is. During their adventures across Skyrim, the Arrow begins to develop his own feeling of attraction for Serana, and vows to protect her, as long as she stays with him. She incidentaly informs the Arrow that she made the same vow to herself. As they prepare to travel to the Soul Cairn, the Arrow finds out the painful way that he needs to be "dead" to enter the Cairn. Serana offers to turn the Arrow into a vampire, informing him that the act is "an intimate act", or putting half of his soul in a soul gem. Because of their feelings towards each other, they proceed with the vampire bite. While in the Cairn, they meet Valerica, she questions the Arrow's intentions. He claims that he will protect Serana, and she in turn defends him from her mother. They continue through the questline together, after the Arrow is forced to cure the vampirism by Isran, and attack Volkihar, kill Harkon, and rescue Valerica from the Cairn. The Arrow wears the Amulet of Mara, to show his affection for Serana, in hopes to marry her, she declines because of her fear of temples due to her past. They then stay together, even though she fears the temple, as though they were married, just without the ceremony. (I personally didn't cure Serana's vampirism, since her eyes look cool as a vampire, and really weird as a cured vampire.)
