I'm not sure what a "should win" game is, and "underdog" covers a lot of territory. A three point dog is a lot different than a 14 point dog. I don't think it's realistic or necessary, right now, for us to win games where we're a significant underdog. We've just got to find a way to six wins this year.
At the midpoint of the season it's likely we'll be sitting at 4-2. We'll then need to secure two more victories in the final six. 6-6 and a bowl would signify progress this season, and serve as a nice springboard to another banner recruiting class and a higher W/L ceiling in 2020.