I think there's two particularly good points here. One is that just meeting Tucker's arb ask doesn't move the needle on him signing an extension later. No one picks a particular airline because they have the best snacks.
The other is about the perceived animosity created by haggling and I think it's reflective of how we tend to look at these relationships in a flat, un-nuanced way. Tucker is new to the Cubs so he hasn't built up a relationship, and this act moves the needle from neutral to negative. Ian Happ had many years with the Cubs so the lost equity from going to arb still left the relationship ledger in the positive and facilitated an extension. But that's not how relationships work in practice, where potentially small slights hurt more from someone you're close to compared with someone who you just met. Even if I were sensitive about a particular point, I'd be far more likely to chalk it up to a misunderstanding with someone I had just met compared to a close family member.
The last nod I'll make at this point is that we are talking about humans, and we are not known for our rationality in all circumstances. Going to arb is likely a nothingburger in most cases, but possibly not all. That said, everything we know of Tucker doesn't seem to point to the case, whereas I might have a greater concern if it were, say, Marcus Stroman they were trying to woo long term.