Good topic Jesse.
And it sounds like I'll have to un-ignore Old Dirty and start to read his posts once again. Nice!
I've never used a Kboom, but I've had a good grasp on what it would be like making the picks with one. Frankly, a lot of "no brainer" picks I do with crane work, I set up the rigging visualizing using a Kboom. (Practice for my own Kboom).
The thing that I don't like is, there seems to be a little more up and down climbing to set the multiple slings. And that adds time.
As with most who use a load line, on a stick boom, it is easy to use 1 choker most of the time. Using 2 is satisfactory as well. It is rare (if the picks are planned well in advance) to use/need more than 2 with a stick boom.