Your plan doesn't work, unless you plan on getting Elenwen outiside of the city; when you enter Solitude, Roggvir is about to be executed, so two heads will be rolling before you touch Ondolemar.

Though with the Thalmor nearby, simply wearing his amulet of Talos would be grounds for an execution.

Personally, I prefer siding with the Alik'r. This is partially due to the fact that, frankly, it's easier to hand her over to the Redguards than to slaughter them all, and the fact that she threatens you with a knife doesn't really help her case.

Does this make me a peasant lord?

"they have an Elder Scroll"... Has to be Dexion.