Ok so I've mixed a bit of what has already been said with some of my own ideas. For one, I still doubt that Sigismund II could have children, even if he'd married Christina of Denmark, so I've left them childless. Also, if Bona doesn't suffer the accident that made her lose her second son, it seems likely to me she'd probably try for more children, so I've given her one more before ending it, giving us another daughter to work with. Other than that, I've tried to give everyone pretty believable offspring.
OK, although it looks strange, that Anna d'Este have kids so late, I think her first children would be born during early 1550s. And Bona's son, who died as result of that hunting accidedt, was not named Wojciech, that is translation error-name of Saint Wojciech was translated to Latin as Adalbertus, thus in some sources Bona's son is mistaken for Wojciech, when in fact he was baptized as Olbracht (after Sigismund's brother and grandfather)-that is, rarely used today, form of name Albert, derived from German Albrecht. Albert is also Latinized as Albertus or Adalbertus, thus mistake appeared.
 
OK, although it looks strange, that Anna d'Este have kids so late, I think her first children would be born during early 1550s. And Bona's son, who died as result of that hunting accidedt, was not named Wojciech, that is translation error-name of Saint Wojciech was translated to Latin as Adalbertus, thus in some sources Bona's son is mistaken for Wojciech, when in fact he was baptized as Olbracht (after Sigismund's brother and grandfather)-that is, rarely used today, form of name Albert, derived from German Albrecht. Albert is also Latinized as Albertus or Adalbertus, thus mistake appeared.

I assumed that Anna d’Este might marry him as her second husband, as she did OTL with the Duke of Nemours after the death of the Duke of Guise. A second son doesn’t need to marry immediately, particularly since Sigismund is already married and it isn’t obvious he won’t produce a child. Thus, I sort of constructed a scenario in my head where Prince Albert is in France for whatever reason (his nephew is King of France so it isn’t that unusual) and in that visit he meets a newly widowed Anna and marries her, with his brother’s permission. Sigismund seems like the type to be a little petty and jealous, so a marriage to a widow who might be keep his younger brother in France for a while longer would probably go well. They probably make their way back to the Polish Court sometime after the birth of their first child, and it goes from there. Also I’ve seen both versions of the name (both Wojciech Olbracht and just Olbracht) so I just went with Wikipedia.
 
I assumed that Anna d’Este might marry him as her second husband, as she did OTL with the Duke of Nemours after the death of the Duke of Guise. A second son doesn’t need to marry immediately, particularly since Sigismund is already married and it isn’t obvious he won’t produce a child. Thus, I sort of constructed a scenario in my head where Prince Albert is in France for whatever reason (his nephew is King of France so it isn’t that unusual) and in that visit he meets a newly widowed Anna and marries her, with his brother’s permission. Sigismund seems like the type to be a little petty and jealous, so a marriage to a widow who might be keep his younger brother in France for a while longer would probably go well. They probably make their way back to the Polish Court sometime after the birth of their first child, and it goes from there. Also I’ve seen both versions of the name (both Wojciech Olbracht and just Olbracht) so I just went with Wikipedia.
Olbracht (who normally should be born in February 1528) should inherit Bona's Italian possessions-Bari and Rossano, he'd be send to Italy after reaching age 17-18, before father's death. Being Italian duke he'll need Italian wife and Anna d'Este seems to be good candidate agewise.
 
Olbracht (who normally should be born in February 1528) should inherit Bona's Italian possessions-Bari and Rossano, he'd be send to Italy after reaching age 17-18, before father's death. Being Italian duke he'll need Italian wife and Anna d'Este seems to be good candidate agewise.

Should is the key word, and I can see Bona pushing for that to happen, maybe attempting to see if their connections in France will be any help. But until Olbracht has some sort of actual holdings (and if they're fighting against the Hapsburgs, that might take a while) then he probably won't get a bride. I can see Renee of France refusing Anna for Olbracht over the Duke of Guise initially, even if there's some sort of emotional connection to them. Even if Olbracht is in France in order to curry support for a offensive to get him the Sforza holdings (and remember, Francis I has a daughter left at this point who he'll probably dangle as a prize if Olbracht can take Milan, thus negating an Italian bride for the time anyway), there's a likely chance that it comes to nothing, and from that, I can see him in 1563, at age 35, tired of fighting, with minimal support (and remember, his brother's wife is Hapsburg-adjacent and probably is cautioning Sigismund Augustus from going against the Emperor, his nephew, when it comes to Italy) giving up and just marrying the wealthy widow of the Duke of Guise, a woman who was probably considered for him in his more glorious youth. It'd be up to the person actually writing the timeline, but that's sort of how I saw the scenario playing out. The Polish Prince, promised so much by his mother, brother and sister's father-in-law, jumping at the chance to take on Italy, but ultimately failing, France having made it's deals with the Hapsburgs, and thus falling back into a safe relationship and returning home, to live at his brother's expense before an early death.
 
Olbracht as Duke of Bari and Rossano would be neither landless or poor (Bona after returning from Poland to her lands was able to lend 430 000 ducats to Philip II of Spain, he'll find wife among Italian ducal Houses, if not in Ferrara then in another duchy.
 
Should is the key word, and I can see Bona pushing for that to happen, maybe attempting to see if their connections in France will be any help. But until Olbracht has some sort of actual holdings (and if they're fighting against the Hapsburgs, that might take a while) then he probably won't get a bride. I can see Renee of France refusing Anna for Olbracht over the Duke of Guise initially, even if there's some sort of emotional connection to them. Even if Olbracht is in France in order to curry support for a offensive to get him the Sforza holdings (and remember, Francis I has a daughter left at this point who he'll probably dangle as a prize if Olbracht can take Milan, thus negating an Italian bride for the time anyway), there's a likely chance that it comes to nothing, and from that, I can see him in 1563, at age 35, tired of fighting, with minimal support (and remember, his brother's wife is Hapsburg-adjacent and probably is cautioning Sigismund Augustus from going against the Emperor, his nephew, when it comes to Italy) giving up and just marrying the wealthy widow of the Duke of Guise, a woman who was probably considered for him in his more glorious youth. It'd be up to the person actually writing the timeline, but that's sort of how I saw the scenario playing out. The Polish Prince, promised so much by his mother, brother and sister's father-in-law, jumping at the chance to take on Italy, but ultimately failing, France having made it's deals with the Hapsburgs, and thus falling back into a safe relationship and returning home, to live at his brother's expense before an early death.
Can not see any reason for which Albert of Poland will have trouble to claim his mother's inheritance as the Duchies of Bari and Rossano were in OTL in possession of Bona until her death so Albert as heir will be sent there and Anna will be asked from the start for him as his brother had been offered Kristina of Denmark (who as widow of his mother's cousin can be used to reinforce his claim to Milan)... Bona's italian lands were hers and were rich enough to make Alberto attractive at least as the duke of Guise as husband for Anna d'Este (and really I can not seeing one valid reason for choising Guise over him) and if him istead of his brother will try to reconquest Milan well his wife's connections would be useful for trying to reclaim the Duchy.
 
I decided to replace Christina with her sister Dorothea as wife of Sigismund Augustus, IOTL both were childless, so they'll be ITTL. Bona's child after Olbracht/Albert also is possible, although considering Sigismund I's age, not very likely, but let's give them little Barbara, born in 1530. So now we have:
-Hedwig (Jadwiga), married to Ferdinand
-Isabella (Izabela) married to Dauphin
- Sigismund Augustus (Zygmunt August), married to Dorothea of Denmark
-Anna, married to Albert of Bavaria
-Catherine (Katarzyna), married to Charles Victor of Brunswick
-Albert (Olbracht/Alberto), married to Anna d'Este
-Barbara, married to John George Hohenzollern, Elector of Brandenburg, or to Albert Hohenzollern, Duke of Prussia (rather the former, Albert certainly would be interested, but as first cousin and former clergyman he'll be problematic candidate, and due to fact, that Hedwig never married Joachim II there is stronger need for Jagiellon match with Brandenburg Hohenzollerns).

Surviving brother and different wife means great changes in life of Sigismund Augustus-Bona would not be as overprotective as IOTL. Healthly first wife means, that Sigismund would not be able to remarry (Dorothea lived untill 1580, and there is no chance to get annulment, Dorothea is Emperor's niece and Sigismund Augustus is not Henry VIII, he'll not risk religious conflict to be able to get new wife, especially considering the fact, that he had male heir already)), Barbara Radziwiłł may appear in his life, but would be only his mistress, not wife. So Sigismund's conflict over Barbara with rest of his family and with nobility of both realms would be avoided. King, who has mistress is nothing unusuall, unlike non-dynastic marriage from love. Bona would dislike Dorothea, blaming her for lack of children, but there is spare son, who'll have large family with Anna d'Este, so future of Dynasty is safe. Olbracht, after spending most of his life in Italy, would face serious problems after ascending the thrones of Poland and Lithuania, being almost foreigner not very familiar with political landscape.
 
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Albert or Olbract can marry Lucrezia Maria instead.
Can not see any valid reason for that as Albert was older than Anna and his mother would likely try to secure Anna for him from the start (and another princess, likely Dorothea or Christine of Denmark for her eldest son).
Francis, Duke of Amaule and future Duke of Guise against Albert of Poland, Duke of Bari lose on all the line (Albert is a ruling Duke and the brother of a King while Guise is just a french prince étranger, the brother of a queen consort/regent and a distant cousin of a ruling Duke and uncle of the future Dauphine/Queen of France) and neither of them is poor. I think more likely who Olbracht marry Anna d'Este, Lucrezia Maria the Duke of Guise and Eleonora the Duke of Urbino
 
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Can not see any valid reason for that as Albert was older than Anna and his mother would likely try to secure Anna for him from the start (and another princess, likely Dorothea or Christine of Denmark for her eldest son).
Francis, Duke of Amaule and future Duke of Guise against Albert of Poland, Duke of Bari lose on all the line (Albert is a ruling Duke and the brother of a King while Guise is just a french prince étranger, the brother of a queen consort/regent and a distant cousin of a ruling Duke and uncle of the future Dauphine/Queen of France) and neither of them is poor. I think more likely who Olbracht marry Anna d'Este, Lucrezia Maria the Duke of Guise and Eleonora the Duke of Urbino

Wasn't Lucrezia originally supposed to marry the duc de Nemours, and then Anna's husband died, so Nemours married her instead (despite already being married to Françoise de Rohan)?
 
Meanwhile Charles V is short of nieces-there is one Christina, when Duke of Milan and Elector Palatine have no wives.
Either he do not marry his niece to a protestant or the Duke of Milan will marry an older princess...
I am the only one who think Bona will offer a surving Anna or Isabella to her cousin Francesco II Sforza as next Duchess of Milan? They are both older than Christina and Dorothea and will reinforce his claim to Milan (and have some chances to give him an heir before his death, specially Anna)...
 
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Wasn't Lucrezia originally supposed to marry the duc de Nemours, and then Anna's husband died, so Nemours married her instead (despite already being married to Françoise de Rohan)?
I do not know about that story but as I said Anna d'Este will the Duchess of Bari and Rossano, Lucrezia can be the Duchess of Guise (and maybe then marry Nemours) and Eleonora can marry either Nemours or the Duke of Urbino
 
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