"It's optimistic to think that things will settle out to begin with." Is he being a little pessimistic about this? Yep. But this whole kerfuffle with the City seems like it won't shake out until someone dies somehow and someone else's forces attack in retaliation and things continue until the City's nothing but ashes.

"You don't have to stay in the City," Strange points out. "You could always stay in Didymos."

There's an unspoken 'with me' in there.