Yeah, I think sometimes the job requires thinking fast on your feet, making do with what you have/know, and that leads to some sloppiness; you don't always have the time for careful planning. The demon is longterm, but as confrontation happens, as things change, movement becomes short-term again.

And I i think that a lot of how John was in this episode is making me rethink him.

So many people seemed to decide "how John was" based mostly on a single flashback, and what the boys had to say about him. It's interesting, in fannish tropes Dean is the one who would usually be seen as Speaking Truth, as the character that fans just bought what he sold wholesale without a thought to the unreliable narrator view, where Sam is the less-loved, in some ways, but it's his view of John that often seemed to get bought wholesale. It's like... where Sam&Dean are concerned, Dean speaks the "truth" of their relationship, but where John&the boys are concerned, Dean's overwhelmed by hero worship and alienated Sam speaks the truth. What IMToD seemed to do is give us concrete "shown" evidence that neither boy is entirely reliable/has a complete view of things, anymore than any of us is/does, and shown us that other side of John the loving father that some of us assumed was there, but complicated by the circumstances of his life.

The John post-IMToD is a more complete person than we'd really been able to see before.