The Marauders generally passed off what they did as jokes, and apparently had no ambitions beyond having fun in the moment.
I think that is one of Albus's parameters when deciding who deserves a real chance and who is just the pawn in his game. Ever since Dumbledore became Headmaster, we see this negative push back towards ambition- advanced texts available to Tom are no longer in the library in Harry's time, departments are cut down... Heck, the HBP is the epitome of this- Albus has to re-employ Toastmaster leader to mine him for information he might need to defeat his ex-student.
Remus not being loyal to Albus might look like he is slowly rolling back to savage werewolf habits- especially he spends a decade away from Albus good influence! Surely some social backlash will get him on a good road! And if Dumbledore gets benefits from it... well, that is plus good!
I agree with your interpretation of Sirius-Albus relationship. It would work well even after PoA- Albus possibly constantly guilts himself over his relationship with Gellert, and it helps him "staying on the right patch". So Albus keeping Sirius locked up in OotP could be his way of rehabilitating him(?).
Again Albus perceives guilt as a good tool for redhibition (after all, it works for him!), so his outright toxic behaviour towards poor Severus could be his way of trying to reform him into a normal citizen :/
IMHO Tom was a potentially useful and uncomfortable reminder of what Albus could have become- both Tom and Albus' father leashed out onto muggles when they threatened what was important to them. I think when Tom killed Myrtle in Albus' categories, he jumped from useful and redeemable to useful and to get rid off. Heck, it's quite possible that even if Tom was a normal kid, Albus' opinions would have boxed Tom into certain choices.
The thing that bothers me about Voldemort's operations is the scale. One of the techniques spies, terrorists and freedom fighters is the rule of 3- you group up to 3 people in the cell, and they might know about up to 2 more people from the other cell but no more. This way, if you catch 1 spy you get info about a 3 more people. If you want to get more info you need to hunt down other members of the cell and usually this isn't easy task. Yet in the books during Voldie war 2 it seems everybody knows Severus is spy (or it's Harry's Pov's influence) We don't know how Voldemort organised his spy operations during his first run, but you don't keep your spies and soldiers in the same room- spies are always trained to gather info, so in case the enemy catches them, they are always the last people you want knowing anything about your troops. So us not knowing about any spies other than Peter and Severus could be a good thing or a bad thing.
Conclusion to this comment- Wizarding world is in dire need of therapists
Barty Junior's role may also have originally been as a spy (and possible future assassin), given who his father was. But this wasn't ever confirmed.
You really have to wonder what kind of sloppy organization Voldemort was running that Karkaroff knew the identities of two Death Eater spies. Okay, he maybe stood next to Severus during the (presumably infrequent) meetings of the full circle, and could have recognized him if he ran into him elsewhere. Or if Severus ever served as a DE Healer and treated Karkaroff. But Rookwood?
Did Karkaroff's cell report to Rookwood for some reason, maybe to carry out assignments Rookwood devised based on his spying? (Blackmail this guy to do X, kill that guy...) This doesn't seem like a great plan, and Voldemort also seems like he would prefer to get the information and give the assignments rather than delegating, so it doesn't seem likely.
Maybe it has to do with whatever position Karkaroff held? We don't even know whether he was British-raised, an immigrant, or only went to Britain to hang out with Voldemort after being recruited on the Continent, so that's no help. Maybe he was some kind of diplomat who mostly hung out with the International Wizarding Cooperation employees but met Rookwood at Ministry events. If he had been in proximity to Rookwood while masked and hooded and was an observant person, maybe he could have recognized him that way. (Height, stance, body language, choice of cologne...)
ETA: But still, the question about other spies in the Order is something we'll probably never know. Maybe Voldemort wanted a backup spy in the Order and just failed to manage it. Or he had one who successfully went undetected but also maybe didn't uncover much that was useful. Could be anything!
Dumbledore could try to crush others' ambition because he doesn't want the competition, though. And he'd be clever enough to cloak it as guilt-driven and an attempt to prevent future Dark Lords which had unfortunate side effects even if he didn't actually feel guilty and actually wanted to have a Dark Lord around to look good opposing. I haven't been able to definitively rule out this "remorseless and totally calculating" scenario.
Or he could also both feel guilty and want to crush competition so he'll always be the best (possibly without ever fully admitting the latter to himself). Which impulse would predominate at any given time, I wonder?
I think that is one of Albus's parameters when deciding who deserves a real chance and who is just the pawn in his game. Ever since Dumbledore became Headmaster, we see this negative push back towards ambition- advanced texts available to Tom are no longer in the library in Harry's time, departments are cut down... Heck, the HBP is the epitome of this- Albus has to re-employ Toastmaster leader to mine him for information he might need to defeat his ex-student.
Remus not being loyal to Albus might look like he is slowly rolling back to savage werewolf habits- especially he spends a decade away from Albus good influence! Surely some social backlash will get him on a good road! And if Dumbledore gets benefits from it... well, that is plus good!
I agree with your interpretation of Sirius-Albus relationship. It would work well even after PoA- Albus possibly constantly guilts himself over his relationship with Gellert, and it helps him "staying on the right patch". So Albus keeping Sirius locked up in OotP could be his way of rehabilitating him(?).
Again Albus perceives guilt as a good tool for redhibition (after all, it works for him!), so his outright toxic behaviour towards poor Severus could be his way of trying to reform him into a normal citizen :/
IMHO Tom was a potentially useful and uncomfortable reminder of what Albus could have become- both Tom and Albus' father leashed out onto muggles when they threatened what was important to them. I think when Tom killed Myrtle in Albus' categories, he jumped from useful and redeemable to useful and to get rid off.
Heck, it's quite possible that even if Tom was a normal kid, Albus' opinions would have boxed Tom into certain choices.
The thing that bothers me about Voldemort's operations is the scale. One of the techniques spies, terrorists and freedom fighters is the rule of 3- you group up to 3 people in the cell, and they might know about up to 2 more people from the other cell but no more. This way, if you catch 1 spy you get info about a 3 more people. If you want to get more info you need to hunt down other members of the cell and usually this isn't easy task. Yet in the books during Voldie war 2 it seems everybody knows Severus is spy (or it's Harry's Pov's influence)
We don't know how Voldemort organised his spy operations during his first run, but you don't keep your spies and soldiers in the same room- spies are always trained to gather info, so in case the enemy catches them, they are always the last people you want knowing anything about your troops.
So us not knowing about any spies other than Peter and Severus could be a good thing or a bad thing.
Conclusion to this comment- Wizarding world is in dire need of therapists
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You really have to wonder what kind of sloppy organization Voldemort was running that Karkaroff knew the identities of two Death Eater spies. Okay, he maybe stood next to Severus during the (presumably infrequent) meetings of the full circle, and could have recognized him if he ran into him elsewhere. Or if Severus ever served as a DE Healer and treated Karkaroff. But Rookwood?
Did Karkaroff's cell report to Rookwood for some reason, maybe to carry out assignments Rookwood devised based on his spying? (Blackmail this guy to do X, kill that guy...) This doesn't seem like a great plan, and Voldemort also seems like he would prefer to get the information and give the assignments rather than delegating, so it doesn't seem likely.
Maybe it has to do with whatever position Karkaroff held? We don't even know whether he was British-raised, an immigrant, or only went to Britain to hang out with Voldemort after being recruited on the Continent, so that's no help. Maybe he was some kind of diplomat who mostly hung out with the International Wizarding Cooperation employees but met Rookwood at Ministry events. If he had been in proximity to Rookwood while masked and hooded and was an observant person, maybe he could have recognized him that way. (Height, stance, body language, choice of cologne...)
ETA: But still, the question about other spies in the Order is something we'll probably never know. Maybe Voldemort wanted a backup spy in the Order and just failed to manage it. Or he had one who successfully went undetected but also maybe didn't uncover much that was useful. Could be anything!
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Or he could also both feel guilty and want to crush competition so he'll always be the best (possibly without ever fully admitting the latter to himself). Which impulse would predominate at any given time, I wonder?
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