Glad to see you're persisting, Dustin. For all the talk I see about "visualization" and such, I've often seen resistance here to posts concerned with actually thinking about composition and equipment and shooting specifications -- and what the intention was when a shutter was actuated. I strongly believe it's worth discussing.
You're example this time was so much like one I did last fall that I decided to share it -- and reinforce you're points about lens selection and background and bokeh.
There's a tree across the street from my apartment. The arborists among us will have to say what it is; I'm not oriented that way. The leaves take on a great golden, orangish glow in autumn. In 2012 I took some shots of the leaves in their full color using a 135mm lens to isolate and do a sort of portrait of one or more leaves. I got an adequate shot, but it wasn't as good as what I wanted, so it bothered me all the following year. Last fall (2013) I was determined to get a better rendition -- as our Jewish friends say, "Next year, in Jerusalem."
The right day came in early November, and I went out in late afternoon with the 135mm mounted on the 5D3. The background leaves can provide a great bokeh with the 135 at wide aperture, and I took a bunch of those. One problem becomes DOF when you have to look up into the tree. The angle is not head-on to the leaf you're using as a subject so you need a larger DOF to get the majority of the leaf in focus. Narrowing down the aperture to accommodate DOF then degrades the bokeh somewhat. Not having a ladder to get a head-on shot, I turned my attention to some leaves out on the end of a branch where a portion of blue sky would provide a contrasting background.
I ended up with shots like the one posted here. Most of the target leaf is in focus at f/4.5. That blurs out the sky pretty well so it's just a blue background with a hint of cloud. A wider aperture would not have provided enough DOF given the angle on the leaf. A narrower one would have slowed down shutter speed too much for the breeze that kept the leaves dancing. And finally, there were banks of clouds moving across the sun -- so much persistence was needed waiting for the right light and a break in the breeze.
Specs on this image: 5D3, Canon 135L, f/4.5, 1/500, ISO 160.
Discussing the decisions made about equipment, composition, specifications, etc. are very useful. For me, this tends to keep all these things in mind when I shoot instead of just looking only at one or two aspects. On a good day, I do a lot less "I wish I had thought about..." when I come home with the images.