WIth all those levels and, perhaps more importantly, Daedric artifacts, I had no difficulty surviving through the battle. Shortly after I killed Alduin, I signed up with the Stormcloaks.Everything went fine until after the Battle of Whiterun, when the civil war began in earnest.
I allowed Elenwen to stay for the conference, which enabled me to give the Stormcloaks a second hold to make up for it.
The first time I tried it, Stormcloak side, I didn't start until after I'd killed Alduin, meaning I'd completed Season Unending in the process.