So, I would say that this is kind of a mild weakness. Sure it's annoying, it just keeps coming back! But, it's not too hard to get rid of it. Just commit it to a test that you know you're going to fail anyway (It's pretty hard to succeed with a modified stat of 0). Conversely, if you've already got a full hand and a couple Pickpocketing (2) or Lucky Cigarette Case in play, just ignore it, and continue to succeed by 2 anyway. Eventually you'll draw an which will hurt your tempo, for sure, but at least you no longer have to worry about Arrogance. That is, until you inevitably cycle your deck again.

That's been my experience with this, so far, anyway.

Posting a ruling clarification from Matt here.

My Question:

In the scenario City of Archives, Act 3a Repossession reads, "Action: Spend 1 clue: Draw. Draw 2 cards instead of 1. If your hand exceeds your maximum hand size, draw 1 additional card." Question 1: Let's say my max hand size is 4. If I have 3 cards currently in my hand, and I trigger the action on the act, do I draw 2 cards, or do I draw 3 cards? In other words, when is the condition "If your hand exceeds your maximum hand size" being assessed? Question 2: If the additional card applies to this draw. Are the 3 cards drawn simultaneously, or am I drawing 2 cards, and then drawing one more card? In other words, is this one draw effect or two draw effects? This matters for some cards such as Amnesia. Thank you!

Answer from Matt Newman:

It is all one draw effect—you draw 2 cards, plus 1 additional card if your hand exceeds your maximum hand size. (In your example, you would only draw 2 cards, because your hand size does not currently exceed your maximum hand size.) Hope that helps!

I was thinking about a deck that could make Winchester work (Jim Culver), and here are my thoughts about it:

1. Additional damage is unreliable if you don't have a way to fish for tokens. Even then, you are wasting too much resources and cards to make it work (Dark Prophecy for example).
2. The card requires 2 hands, so it requires 100% commitment. Overall, the card would be great if it said "if a token with +1 or 0 MODIFIER is revealed". This way, Jim's skulls counted as 0s would proc the effect and additional modifiers from the scenarios would work as well (e.g. X, where X is the number of doom in play with 0 doom in play).

For each point you fail by, take 1 horror. Sentence quite scary since Rotting Remains first revelation. Vast Expanse can be less scary than Rotting Remains, it can be exactly like Rotting Remains but if there is a lot of extradimensional locations in play, its effect can be even worser. Autofailing (5) can end your campaign easily. My own experience. Everything was very good, all Rex needs was to survive mythos phase and resign. It never happened...

Two additional janky situations:

• Have Open Gates in two characters. Then the card does not only skip backtracking, but let's you skip parts of the map. Some copies might be useless, though.
• Play an Open Gate with "You owe me one" from the hand of your friendly neighborhood mystic. You can do this from the other side of the map. Sure, it's not fast anymore, but enables you to reunite your party. Played this in Lost in Time and Space to pull the Akachi of the team to the top as Mandy.