Step 5: Execution!
This worked beyond my expectations. The neck of the bottle is stiff enough that I could tug down on the fruit and the stems would snap, the shape of the bottle made it pretty easy to slip between branches, and the pole makes for easy access to those fruit that dare defy you by growing out of arm's reach. In fact, I was so pleased with the ones I managed to get that I went back and screwed an extension to my pole since I had another piece of wood laying around. Beware, fruit picking can be addicting, I was tempted to add a third extension because trees have a bad habit of growing tall, but I might have to rein myself in.
If had free access to custom materials, I'd probably make a sturdier "basket" for grabbing the fruit, there were a few times where it collapsed and popped back out again when I was trying to get at some difficult pears. An extendable pole would be quite handy, or even a hollow pole that would let the fruit slide down to you, but that could be more unwieldy than the basket method, especially if a fruit got stuck.
In any case, I hope you enjoyed my first instructable!