S1 - Ben’s so fixated on the idea of traitors in the Continental Army that he makes a futile effort to gain information from someone who could not possibly provide it. He never verbally considers potential consequences, and it comes back to bite him both short-term (Scott) and long-term (Simcoe’s continued, you know, life, in general. Caleb. Everything, really.)

S1 - After Andre’s codebook clues everyone in to enemy schemes, Ben’s so fixated on the information right in front of him that he doesn’t realize Washington’s made the appropriate plans until Washington explains that he’s planning a counter-feint.

S1 - Ben’s so concerned with rescuing family and friends in Setauket that he goes against orders and potentially risks major consequences (loss of life, disrupting Abe and Anna’s work as spies) to do what he believes is right. Technically it does save lives, his father’s included, but there are casualties.

S2 - Ben’s so fixated on the disrespect toward Washington that he picks a fight with an Officer who outranks him, an action which could have brought serious repercussions for everyone involved in the fight if anyone had chosen to acknowledge it.

S2 - Ben’s so fixated on the disrespect toward Washington and on Lee’s treachery that he never considers the potential consequences of exposing Lee, even after Washington touches on the subject (telling him it would lower the army’s morale, nevermind the issues with the French), and proceeds to commit a string of crimes to obtain evidence despite Washington’s directions to the contrary.

S2 - The Sutherland-Shanks debacle has Ben doing his utmost to consider all angles, but it’s an impossible position; he isn’t completely wrong, and Washington is far from completely right, but Ben’s earlier errors contribute to Washington taking the matter out of Ben’s hands.

S2 - With the arrests of Hickey and Bradford, Ben lays out a case for how they should be dealt with, his commentary on the matter showing direct contrast to his thoughts and actions regarding Lee. This time, he’s accounted for everything.

S3 - There is a deleted scene which doesn’t appear to be entirely canon, having been broken up and the pieces moved throughout the season, in which Ben takes a step backward in his pragmatism and refuses to carry out the very plan he’d proposed of writing Bradford and Hickey off as mere Counterfeiters, leaving Washington to write up the final reports instead as Ben can’t reconcile the necessary measures with his conscience.

S3 - Ben’s so fixated on Reverend Worthington’s betrayal...he accounts for the fact that they can’t formally execute him without arousing suspicion, but again he’s so wrapped up in his emotions on the matter that he ignores (and admittedly, so does Washington) Caleb’s suggestion of at least holding back and finding out the logistics of Worthington’s operation, such as who’s his contact. Ben’s first and main thought is that he has to kill this man. This is Ben’s first experience with this type of killing; he isn’t in a battlefield setting, he’s not killing in direct self-defense. Reverend Worthington is unarmed. Further, it’s in another moment of heated emotion that Ben actually pulls the trigger- a knee-jerk reaction to a slight against Washington. He’s noticeably unsettled as he disposes of the body, and too distracted to consider any threat until Gamble has him at gunpoint.

S3 - It’s suggested off and on, and is touched on during the Sarah Livingston Debacle, that Ben’s so wrapped up in his belief of The Cause that he kind of...hasn’t considered that his side can be every bit as capable of horrible things as the enemy. He’s genuinely shocked as Sarah tells him it was Continental soldiers who killed her husband, all but on Washington’s orders.

S3 - Ben’s so focused on the Counterfeiting Fiasco it doesn’t occur to him, or anyone really, to think of what the counterfeiters will be doing with the money until Anna points it out. I have Other Issues with this particular plot point but it does fit with Ben’s tendency to miss the bigger picture at times.

S3 - Obviously also, Ben walks in on the aftermath of Sarah’s murder, he sees the scratches on Randall’s face and never once considers proper protocol...he’s all emotion and attacks Randall without any regard for potential consequences. For some reason the series touches on it enough in S4 to say things went in Randall’s favor, but not enough to point out that, in reality, Ben could have lost his position over this.

S3 - He just, exhibits, throughout, this black-and-white thinking that Patriots are Good, Loyalists are Bad. He holds Nathan to one standard and the enemy’s operatives to another, and doesn’t really seem to reconsider that belief at all until around the time of Andre’s execution while Arnold’s defection is still weighing on him. But he does start to wrestle with it.

Now, disclaimer that I still haven’t actually seen S4 and so don’t pretend to know what the hell I’m actually talking about, but from what bits and pieces...it seems to me that there comes a point, including with dealing with Caleb, however horrible it was to watch, that Ben reaches a point where he goes from overlooking the bigger picture, to looking pretty much only at the bigger picture. He might still fall into his same patterns from S1-S3 at times (and probably does. Such as when he doesn’t want to risk asking Caleb to do something and so intends to do it himself, despite that being a horrible idea and despite Anna’s warning) but there’s a shift. That shift includes choosing between being a good friend or trying to be a good soldier. He chooses the latter. That shift includes tolerating rumors of his involvement with a married woman. (a very minor issue, yes, considering we’ve never seen him concerned with his own reputation as much as Washington’s) That shift includes presenting, at times, as overly, and aggressively pragmatic, and it includes a shouting match with Washington in a near-reversal from S2.

Ben got character-development, between these examples and, of course, other things over the course of the series. It didn’t show up prettily and it wasn’t always necessarily obvious, but it was there and I think a lot of what didn’t make sense actually did, however hard it was to watch play out at times.