No, his strategy doesn't fall apart at all, you simply factor in the increases too. Players understand that part.
Players can understand Cobb making nearly what Nelson does, perhaps just a slight bit more. They might not understand the idea of Cobb making $11M or more.
I think the idea of players taking anything significantly less to sign early is antiquated, at best. All it does is anger them a year or two later At best, signing early gives the team a bit more freedom to manipulate cap hits, but the players still (mostly) expect whatever would be fair if they were in fact a FA at the time