Is anyone covering Westerkamp in this picture? He looks quite open. I'd go for the corner of the end zone too.
Another thing is QBs don't have the luxury of deciding between two options (at least, I don't think they do.) Not usually. When you go through progressions, you take the first one if it's there, and if you move on to the second you probably don't come back to the first. And you might not have time to go through progressions, especially if you're a young QB.
In the last screen, a better throw as Tommy made on a previous out to either Westerkamp or Jamal seems like it should have done the job. This throw was not in the right place at all. It does seem like he's fairly tightly covered though, which is what makes the out a difficult throw. You really have to zip it way out there or the risk is substantial.
And I do agree, Tommy should choose to move on from his first progression a little more. Although the decision-making probably goes: if I switch and look at #2, and he's covered, I'm probably taking a sack. Maybe in time he'll do this all fast enough to get to his checkdown as well.