1. It wasn't. Strictly-speaking she didn't have an army, honestly. A better word would be her coven, since it was basically a whole bunch of very powerful witches. Quite a few are still alive, but not exactly good teachers for anyone who's not magical and they're also in hiding.

2. I know that, but IC it's a problem because character-wise he'd probably be kicked out of the party, attacked, or dragged to the courts in Meridan.

3. I will admit there's some Tolkien-esque elements in my setting(though honestly most European Fantasy-based settings have some hints of Tolkien somewhere), but Orodagor's hardly Mordor. It's one fortress, and it wasn't even Hidroroth's "land of evil" or anything like that. It was the furthest southwest fortress that's more notable then others because the Witch-Queen set up her coven there. As for omitting backstory, it's only okay if you really have no backstory in mind. And to be frank I forgot to strip that out of the OP when I was editing it to be reposted.