Leno
As YouTube series "The Tape Never Lies" showed week after week, Leno was not preforming well enough to start. He has limited talent to begin with, and he was not using correct technique nor effort -- and since he's done better, we assume that's an attitude issue... likely worsened by the extension. (Not that the extension was necessarily a bad decision, but we know Leno now.) 2020 Leno should have starting competition, and hopefully be an expensive swing tackle cause we're stuck with him.
Massie is a very similar situation. We're stuck with him 2020.
We should draft one OT in the 2nd, at least; or two if excellent OTs are there. The draftee may take awhile to develop, so you need to see if Free Agency can provide a reasonably priced competitive swing tackle (maybe Lucas is the guy), giving the Bears four OTs, likely 2 of which can play G if required.