Hey Will,
Most new things are at least a little bit intimidating. Don't let that stop you from asking questions and performing experiments though. 
I've asked @peternlewis a couple of times to make the Prompt With List action's sort optional, but he's never committed. If you want that feature then petition for it. The more users who do, the more likely it will come about.
This fabulous macro by @DanThomas has more options than the built in prompt from list.
MACRO: Spotlight Search Prompt
And of course there is the AppleScript method, which is much less powerful but much simpler.
set myList to "one
two
three
four
five
six
seven
eight
nine
ten"
set myList to paragraphs of myList
tell application (path to frontmost application as text)
set myChoice to choose from list myList ¬
with title ¬
"MyTitle" with prompt ¬
"MyPrompt" default items (item 1 of myList) ¬
multiple selections allowed true ¬
without empty selection allowed
end tell
-Chris