Quick followup question: once he replaces the Hegemony with his new empire (or koinon, depending on the playthrough), what’s your MC’s envisioned tax policy?
So far, I vaguely remember that your “all religions can fairly compete with each other” policy involves stripping of the Xthonic priesthood of their tax-exempt status, but are there any other details you’d like to share?
Is it just the reputation for keeping guest right that concerns your MC, or does the reality of putting in the hard work (of consistently upholding guest right/hospitality) also matter as well?
E.g. Might your MC consider occasionally pursuing the ‘Tywin Lannister’ route of outsourcing a Red Wedding-style betrayal to a behind-the-scenes ally? (thus claiming plausible deniability in the process)
Do you think that you can present enough of a “we’re going to be the winning side” impression to win over (pragmatic) Teren in the long run?
(especially if you entertained the idea of your new world order preserving a comfortable balance of power between your meritocratic “new generation” elites and the few surviving “old guard” hereditary aristos who took a chance on allying with your MC)
When you phrase it like that, it gives me high hopes that Elery will support (or at least understand/tolerate) MC’s potential decision to ally with Phaedra in the later games (aka switching gears/goals from tearing down the Hegemony to reforming the Hegemony).
If not for the incompatible genders/orientations, I would have recommended pairing your MC together with Cerlota; these two characters are definitely peas in a pod! (given their shared ruthlessness and Cosmo leanings).
Anyways, what about Yebben? Is he smart/likable enough to be ideal boyfriend material for your MC?
Amplifying your rebellion’s networking/recruitment reach. 
(to a significant extent that couldn’t be achieved by playing safe/merely hiding out in the woods)
If Cerlota tries to bring up the “break a lot of eggs to make an omelette” analogy (as her justification for unleashing a WMD), then my (more cynical and less trusting towards Theurges) MCs will brush her off as “a messy cook.”
Are you planning to drop all of the Hegemony’s existing Wards in favor of your “self-sacrifice Theurgy-powered canal” plan, or are there a few handful that you would like to keep preserved? (e.g. the ward protecting Erezza from Halassur)
Does your MC have any aspirations of making a new empire of his own, or is he happy enough to settle for being a kingmaker when all is said and done?
Your current phrasing seems to suggest the latter, in my opinion.
I tried googling this, and I still don’t understand what the acronym stands for. Could you please clarify?
This past quote from Havie may prove to be relevant: “But even if you fought off the army sent to destroy you in the wilderness, that still leaves you miles from the point where any noble in Grand Shayard would look at you and think “they’re going to beat the Thaumatarchy”. Even sympathizers would still see you as a helpful distraction off on the fringes, depleting a bit of the Hegemony’s strength, rather than the core rebellion. Change comes from power centers, not from the periphery, everyone knows that! (Or at any rate, just about every noble believes that.) And unsympathetic nobles like the de Firiacs wouldn’t even grant you that much respect.”
Eh, last I checked, Abelard didn’t mind. (During the Jailbreak route)
In fact, he goes out of his way to equip your guys with Theurgic spears!
I suspect that the merchants will have mixed feelings about a high-anarchy MC. On one hand, too much anarchy means that the atmosphere is too violent/unstable to safely conduct trade.
But on the other hand, since high anarchy dismantles/weakens the existing institutions of the Hegemony, maybe the merchants also see an opportunity to exploit the chaos to become more wealthy/powerful in their respective post-Hegemony nations.
(perhaps to the extent of supplanting the hereditary aristos to become the new elites of the post-Hegemony nations)
I’d like to see more details about your Game 1 build/decisions before I can advise you on which Game 2 factions would be most compatible with your MC’s vision.