Ahmen!
1. I too have bought a lot of "stupid" stuff. But, what's "stupid" for me might make someone else's day so, I try to pass that stuff along for free as a way of paying it forward.
2. I think we all go through this but, the organization will help with that
3. Even with a Kapex and dedicated CT, this tool tosses the dust! Regardless, I don't see my shop without it. That's right for my shop, could be different for yours.
4. See answer #1. Unless they have some sentimental value, I simply try to move that stuff on to someone who wants to grow with them.