#if ozpin was already friends with leo james and theodore before the reincarnation happened

[strqyr]

if you treat team strq, the headmasters and ozpin as their era's team rwby, team jnpr and oscar (with ozpin pulling double duty as the person who dies and oz reincarnation), by comparing their situations and taking rwby's themes into account, it's easy to see why the older generation failed.

mainly, team rwby and co have been through a lot, and most of it, they've been through it together. they've always had each other for support – and even when team rwby were separated, they still had someone, whether it be friends or family or anyone, really, to help them in any way they needed.

as far as we know, that wasn't the case for team strq and co. we know that raven and qrow acted as spies, meaning they would spent most of their months long missions alone. according to ruby, summer and tai at least went on missions together, but once they had kids to take care of, that would have happened less and less.

the headmasters, by their role alone, were separated, stuck for the most part within their own schools and kingdoms. and from the looks and sound of things, none of them exactly had easy time with their councils, making their life even more difficult.

(and depending how many strings ozpin was pulling to get his friends and allies appointed as headmasters, that may have been the case from the start... not to mention how his status as one of the youngest headmasters ever might have worked against him, too.)

when ozpin dies, unlike team jnpr, who grew closer than ever after pyrrha's death, the remaining headmasters not only grew further apart (if they were close to one another in the first place) but any contingency plans ozpin had for this exact situation were promptly thrown out of the window by at least lionheart and ironwood.

team strq and the headmasters were doomed to fail, not because their personal flaws – not when the younger generation has flaws similar to theirs, though they overcame them thanks to the support they have – but because their system was not actually build around teamwork, relying more on individuals to handle things on their own.

if team rwby and co have struggled to handle the very same things and revelations when they have each other, it's no wonder those very things doomed team strq and co.

though there's also seems to be a split, with so far ozpin the headmaster, lionheart and ironwood dying, while ozpin the wizard and team strq learn from their mistakes and take responsibility for their failures, and help the younger generation not as authority figures, but as equals.