Ugh. My new fear for this quest is having Vainglory make us a slightly less sadistic version of Viserys Targaryen (from Game of Thrones), who was somehow both sad and ridiculous in his attachment to lost respect and tarnished glory. We even have a house whose reputation is reviled in our old homeland, just like him!
We don't have the skillset required to reproduce past military victories, and we likely won't be able to reproduce past political ones either (right now we're looking like someone who dabbles into various sciences, not like a statesman or administrator or whatever).
On the other hand, this vice makes a lot of sense when taken with The Classics, so that's nice.