What do you have in mind, regarding Cupich's "theological shortcomings"? On the basis of this article, I note he seems prepared to accept as "Catholic" those good people whom more stern types might condemn for their doctrinal heterodoxy. And a few of these stern types make their presence known, often enough, among NCR commenters.
I for my part am very glad to consider this attitude of Cupich's a real "sign of hope."