Thanks for the words of advice (and encouragement) guys/gals! How would I go about setting up the "shift" functions that were mentioned here? Is that something I'd do in-game or to the hardware itself?
You can do it both ways in Elite: Dangerous. Most controllers include software that lets you modify how it sends commands to a game. For example, CH's control manager has a "mapped" mode where you can assign a "shift" button, and send various commands, key strokes, macros, and Direct X controls, that way. More expensive controllers (such as CH's hardware, like my CH HOTAS) also can be programmed via their own scripting language. For example, I have a small script that toggles both rotational assist AND my landing gear with a single "shift util-hat down" combo.
You can also do it in-game, when setting up your controller in the options menu. E: D has for some time let you enter two button combos to activate a control.